Substituted phenyltriazolopyrimidine herbicides

ABSTRACT

Novel substituted phenyltriazolopyrimidines and their preparation and method-of-use as preemergence and postemergence herbicides.

RELATED APPLICATION

This application is a continuation-in-part of my copending applicationU.S. Ser. No. 07/335,121 filed Apr. 7, 1989, now abandoned which is acontinuation-in-part of U.S. Ser. No. 07/221,155, filed Jul. 19, 1988now abandoned.

BACKGROUND OF THE INVENTION

U.S. Pat. No. 4,209,621, issued Jun. 24, 1980, discloses substitutedphenyl-1,2,4-triazolo[1,5-a]pyrimidines of the formula ##STR1## whereinR₁ is H or alkyl as anxiolytic agents.

French Patent 1,433,798, published Feb. 21, 1966, (U.S. priority May 1,1964), discloses 7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine as aherbicide.

EP-A-220,458, published May 6, 1987 (German priority Sep. 28, 1985) andEP-A-217,218, published Apr. 8, 1987 (German priority. Sep. 28, 1985),disclose herbicidal triazolopyrimidines of the formula ##STR2##

EP-A-215,382, published Mar. 25, 1987 (German priority Sep. 17, 1985),discloses herbicidal 7-aminoazolo[1,5-a]pyrimidines of the formula##STR3## wherein A is N, CH, C(alkyl) CBr or CCl.

U.S. Pat. No. 4,740,233, issued Apr. 26, 1988, discloses herbicidaltriazolopyrimidines of the formula ##STR4## wherein R₁ includes phenyland substituted phenyl.

J. Fac. Agric. Kyushu Univ. 1977, 21 (2-3), 99-105 discloses herbicidaltriazolopyrimidines of the formula ##STR5## wherein R₁ is H, SCN, SCH₃,Ph or CH₃ ;

R₂ is H or CH.sub. 3; and

R₃ is SH, SCH₂ Ph or SCH₂ CO₂ H.

J. Fac. Agric. Kyushu Univ. 1975, 19(2-3), 91-102 disclosess-triazolo[1,5-a]pyrimidines with herbicidal activity.

The present invention is patentably distinguishable over the foregoingat least in the substitution on the azole and/or the pyrimidinefunctionality.

SUMMARY OF THE INVENTION

This invention comprises compounds of Formula I, agriculturally suitablecompositions containing them, and their method-of-use as preemergenceand/or postemergence herbicides ##STR6## wherein G and G¹ are N or C;

R₁ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄alkenyl, C₂ -C₄ alkynyl,

C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, halogen, CN,

C₂ -C₄ alkylcarbonyl, C₁ -C₄ alkylamino,

C₂ -C₄ dialkylamino or C₂ -C₄ alkylthioalkyl;

R₂ is halogen, NO₂, OR₃, S(O)_(n) R₃, OSO₂ R₃, C₁ -C₄ haloalkyl, C₃ -C₄halocycloalkyl, C₃ -C₄ haloalkynyl or C₂ -C₄ haloalkenyl;

R₃ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkenyl, C₂ -C₄haloalkenyl, C₃ -C₄ alkynyl, C₃ -C₄ haloalkynyl, or C₃ -C₄halocycloalkyl:

R₄ is H, halogen, C₁ -C₃ alkoxy, C₁ -C₃ alkyl or CF₃ ;

R₅ is H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂-C₄ alkenyl, C₂ -C₄ alkynyl, NO₂, OR₃, S(O)nR₃, OSO₂ R₃, phenyl,phenoxy, C₂ -C₄ alkoxycarbonyl, C₂ -C₄ alkylcarbonyl, CN, NHSO₂ CF₃, C₂-C₄ haloalkenyl, C₃ -C₄ haloalkynyl, C₂ -C₄ dialkylamino, or C₃ -C₄halocycloalkyl;

n is 0, 1 or 2;

R₆ is H or F;

X, Y and Z are independently CR₇ or N; and

R₇ is H, CN, halogen, NO₂, CO₂ R₃, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl orCONH₂ ;

provided that (a) G and G¹ are not the same, (b) R₁ is not CN when X isN and (c) only one of X, Y, Z can be CR₇.

In the above definitions, the term "alkyl," used either alone or incompound words such as "alkylthio" denotes straight chain or branchedalkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butylisomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the differentbutoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl,1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl,1-propynyl, 2-propynyl and the different butynyl isomers.

The term "halogen," denotes fluorine, chlorine, bromine or iodine.

The term haloalkyl or halocycloalkyl denotes mono to per-halogentaedalkyl isomers e.g. 1-fluroethyl, 1,1,2,2,2 pentafluro ethane,2.2-diflurocyclopropane.

The total number of carbon atoms in a substitutent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 4. Forexample C₃ -C₄ alkenyl would designate propenyl through butenyl.

Preferred Compounds

Preferred for reasons of increased ease of synthesis and/or greaterherbicidal efficacy are:

1. Compound of Formula I wherein

G is CH and G¹ is N (Formula Ia); or

G is N and G¹ is CH (Formula Ib). ##STR7## 2. Compounds of Preferred 1wherein Formula I is Ia;

X is CR₇ ;

Y is N; and

Z is N.

3. Compounds of Preferred 1 wherein

Formula I is Ib;

X is CR₇ ;

Y is N; and

Z is N.

4. Compounds of Preferred 1 wherein

Formula I is Ia;

X is N;

Y is CR₇ ; and

Z is N.

5. Compounds of Preferred 1 wherein

Formula I is Ib;

X is N;

Y is CR₇ ; and

Z is N.

6. Compounds of Preferred 1 wherein

Formula I is Ia;

X is N;

Y is N; and

Z is CR₇.

7. Compounds of Preferred 1 wherein

Formula I is Ib;

X is N;

Y is N; and

Z is CR₇.

8. Compounds of Preferred 1 wherein

Formula I is Ia;

X is N;

Y is N; and

Z is N.

9 Compounds of Preferred 1 wherein

Formula I is Ib;

X is N;

Y is N; and

Z is N.

10. Compounds of Preferred 8 wherein

R₆ is H; and

R₁ is C₁ -C₃ alkyl, SCH₃, NHCH₃, CHO₂ CH₃ or CH₂ SCH₃.

11. Compounds of Preferred 10 wherein

R₂ is CF₃, SCF₃, SCF₂ H, OCF₃, OCH₂ CHF₂, OCH₂ CF₃, OCF₂ H, CF₂ CF₃, CF₂Cl, CHF₂, CH═CF₂ or 2,2-difluorocyclopropane.

12. Compounds of Preferred 11 wherein

R₃ is CH₂ CH₂ F, CH₂ CF₃, CH(CH₃)CF₃, CH₂ CH₂ CF₃, CH₂ CHF₂, CF₃ or CF₂H; and

R₄ is H.

13. Compounds of Preferred 12 wherein

R₅ is H, halogen, OCH₃, OCF₂ H, OCH₂ CF₃, SCF₃, C₁ -C₃ alkyl, OCF₃, OCH₂CHF₂, OCH₂ CF₃, OCH₂ CH₂ F, SCHF₂, CF₃, CHF₂, CF₂ Cl, CH₂ CF₃, CH₂ F,CCl₃, CH₂ Cl or CN and R₅ is in the meta position.

14. Compounds of Preferred 13 wherein

R₁ is C₁ -C₃ alkyl.

5. Compounds of Preferred 9 wherein

R₁ is C₁ -C₃ alkyl;

R₂ is CF₃, SCF₃, SCF₂ H, OCF₃, OCH₂ CHF₂, OCH₂ CF₃, OCF₂ H, CF₂ CF₃, CH₂Cl, CHF₂, CH═CF₂ or 2,2-diflurocyclopropane;

R₃ is CH₂ CH₂ F, CH₂ CF₃, CH(CH₃)CF₃, CH₂ CH₂ CF₃, CH₂ CHF₂, CF₃ or CF₂H;

R₄ is H;

R₅ is H, halogen, OCH₃, OCF₂ H, OCH₂ CF₃, SCF₃, C₁ -C₃ alkyl, OCF₃, OCH₂CHF₂, OCH₂ CH₂ F, SCHF₂, CF₃, CHF₂, CF₂ Cl, CH₂ CF₃, CH₂ F, CCl₃, CH₂ Clor CN and R₅ is in the meta position; and

R₆ is H.

6. Compounds of Preferred 4 wherein

R₁ is C₁ -C₃ alkyl;

R₂ is CF₃, SCF₃, SCF₂ H, OCF₃, OCH₂ CHF₂, OCH₂ CF₃, OCF₂ H, CF₂ CF₃, CH₂Cl, CHF₂, CH═CF₂ or 2.2-diflurocyclopropane;

R₃ is CH₂ CH₂ F, CH₂ CF₃, CH(CH₃)CF₃, CH₂ CH₂ CF₃, CH₂ CHF₂, CF₃ or CF₂H;

R₄ is H;

R₅ is H, halogen, OCH₃, OCF₂ H, OCH₂ CF₃, SCF₃, C₁ -C₃ alkyl, OCF₃, OCH₂CHF₂, OCH₂ CH₂ F, SCHF₂, CF₃, CHF₂, CF₂ Cl, CH₂ CF₃, CH₂ F, CCl₃, CH₂ Clor CN and R₅ is in the meta position;

R₆ is H; and

R₇ is CN.

17. Compounds of Preferred 5 wherein

R₁ is C₁ -C₃ alkyl;

R₂ is CF₃, SCF₃, SCF₂ H, OCF₃, OCH₂ CHF₂, OCH₂ CF₃, OCF₂ H, CF₂ CF₃, CH₂Cl, CHF₂, CH═CF₂ or 2,2-diflurocyclopropane;

R₃ is CH₂ CH₂ F, CH₂ CF₃, CH(CH₃)CF₃, CH₂ CH₂ CF₃, CH₂ CHF₂, CF₃ or CF₂H;

R₄ is H;

R₅ is H, halogen, OCH₃, OCF₂ H, OCH₂ CF₃, SCF₃, C₁ -C₃ alkyl, OCF₃, OCH₂CHF₂, OCH₂ CH₂ F, SCHF₂, CF₃, CHF₂, CF₂ Cl, CH₂ CF₃, CH₂ F, CCl₃, CH₂ Clor CN and R₅ is in the meta position;

R₆ is H; and

R₇ is CN.

Specifically Preferred for reasons of greatest ease of synthesis and/orgreatest herbicidal efficacy are:

5-methyl-2-(trifluoromethyl)-7-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidine;

7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine;

5-methyl-2-(trifluoromethyl)-7-[3-(trifluoromethyl)phenyl]-pyrazolo[1,5-a]pyrimidine-3-carbonitrile;

5-methyl-2-(2,2,2-trifluoroethoxy)-7-[3-(trifluoromethyl)-phenyl][1,2,4]triazolo[1,5-a]-pyrimidine;

2-(difluoromethoxy)-5-methyl-7-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidine.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

Compounds of general Formula I can be prepared using one or more of thereactions and techniques described in Schemes 1-8 of this section aswell as by following the specific procedures given in Examples 1-15.

Scheme-1 illustrates the reaction of aminoheterocycles of Formula IIwith an appropriately substituted diketone of Formula III to afforddesired compounds of Formula Ia where R₁ is alkyl, alkenyl, alkoxyalkyl,alkyl substituted by halogen and R₂, R₄, R₅ and R₆ are defined as above.This reaction is carried out by heating the reactants neat or in aninert polar protic or aprotic solvent at temperatures between 50° and130° C. Suitable solvents are glacial acetic acid, ethanol, methanol,dimethylformamide, and dimethylsulfoxide. Aminoheterocycles of FormulaII can be prepared by synthetic methods reviewed in "The Chemistry ofHeterocyclic Compounds" Volumes 6 (1953), 22 (1967), and 37 (1981), JohnWiley & Sons. Beta-diketones of Formula III can be synthesized bystandard Claisen acylation procedures such as those taught by C. R.Hauser et. al. in Journal of American Chemical Society 67. pg. 284(1945), 68, pg. 2742 (1946), 69 pg. 2649 (1947) and 70 pg. 4023 (1948).##STR8##

A minor regio isomer Ia' can also be formed in the reaction shown inScheme-1. Compounds of Formula Ia are isolated pure, however, afteraqueous workup, trituration, and subsequent purification byrecrystallization or silica gel column chromatography. Silica gel columnchromatography can also be used to isolate products of Formula Iadirectly from the crude reaction residue obtained after reaction workup. Scheme-2 illustrates the preparation of compounds of Formula Ia(where R₁ is hydrogen, alkylthio, or alkoxy and R₂, R₄, R₅ and R₆ aredefined as above) by reaction of aminoheterocycles of Formula II withcompounds of Formula IV where Q is a suitable leaving group such asdimethylamino, methylthio or methoxy. This reaction is carried out byheating reactants II and IV neat or in an inert polar protic or aproticsolvent such as glacial acetic acid, ethanol, methanol,dimethylformamide, or dimethylsufoxide at temperatures between 50° and130° C. Compounds of Formula IV can readily be prepared by one skilledin the art by known methods. ##STR9##

Scheme-3 illustrates the diazotization of compounds of Formula V(Prepared by the method shown in Scheme-1 where R₂ =NH₂) in an aqueousacid medium of Formula HL (where L is equal to halogen) to givecompounds of Formula Ic where R₂ is halogen and G, G', X, Y, Z, R₁, R₄,R₅ and R₆ are defined as above. Acetic acid can be used as a solvent inthis diazotization reaction to enhance the solubility of V in the acidmedium. The diazotization is conducted intially at temperatures between5° and 25° and subsequently heated at 30° to 100° C. or maintainedthroughout at room temperature. ##STR10##

Scheme-4 illustrates the reaction of compounds of Formula VI (where K isO or S, G', X, Y, W, Z, R₁, R₄, R₅ and R₆ are defined as above) with analkylating agent of formula R₃ -Q' (where Q' is a suitable leaving groupsuch as halogen and R₃ is defined as above) in a polar protic or aproticsolvent such as aqueous dioxane or dimethylformamide in the Presence ofa base such as a metal carbonate, metal hydroxide or metal alkoxide(where the metal is sodium or potassium) at temperatures between 0° and70° C. to give compounds of Formula Id. Compounds of Formula VI can beprepared by the method shown in Scheme-1 where R₂ equals mercapto orhydroxyl. Oxidation of compounds of Formula Id (K is S) with oneequivalent of oxidizing agent such as 3-chloroperoxybenzoic acid, sodiumperiodate, or hydrogen peroxide in a suitable solvent such as methylenechloride (in the case when 3-chloroperoxybenzoic acid is used) attemperatures between 0° and 40° C. gives the corresponding sulfoxidederivatives of Formula Ie (where n is equal to one). Use of excessoxidizing agent under these same conditions gives the sulfonederivatives Ie (where n is equal to two). Substituents G, G', X, Y, Z,R₁, R₄, R₅ and R₆ on Id and Ie are as defined above. ##STR11##

Scheme-5 illustrates the preparation of compounds of Formula If (whereG, G₁, X, Y, Z, R₁, R₄, R₅ and R₆ are defined as above) by reaction ofcompounds of Formula Ic (where R₂ =halogen) with metal alkoxides andmetal haloalkoxides of formula R₃ O⁻ M⁺ (where M=Li, K, or Na and R₃ isdefined as above) by heating in polar protic or aprotic solvents such astetrahydrofuran or dimethylformamide at temperatures between 25° C. and140° C. ##STR12##

Scheme-6 illustrates the reaction of aminoheterocycles of Formula VIIwith an appropriately substituted ketone of Formula VIII (where Q' is asuitable leaving group such as halogen) to afford compounds of FormulaIg (where R₂ is alkyl or haloalkyl). The reaction is carried out byheating reactants VII and VIII neat or in an inert polar protic oraprotic solvent such as ethanol, methanol, dimethylformamide ordimethylsulfoxide at temperatures between 50° C. and 130° C.Aminoheterocycles of Formula VI where X=N can be prepared by methodssuch as that taught by H. G. O. Becker et al., Tetrahedron, 24, 2687(1968). ##STR13##

Scheme-7 illustrates the preparation of compounds of Formula Ih bycyclization of compounds of Formula IX with an acid anhydride or an acidchloride (for R₂ =haloalkyl) or an orthocarbonate (for R₂ =OR₃) astaught by Y. Tamura et al., J. Het. Chem, 12, 107 (1975) and W.Kantlehner, Synthesis, 73 (1977).

Compounds of Formula IX can be prepared from compounds of Formula VII byreagents such as hydroxylamine-o-sulfonic acid, o-mesitylenesulfonylhydroxylamine or o-diphenylphosphinylhydroxylamine as taught by K. T.Potts et al., J. Org. Chem. 31, 260 (1961) and Y. Tamura et al., Tet.Lett. 4133 (1972) and W. Klotzer et al., Synthesis, 592 (1982).

Compounds of Formula IX where X=CR₇ can be prepared by synthetic methodssuch as those reviewed in "The Chemistry of Heterocyclic Compounds",Volume 14, John Wiley and Sons, or known to one skilled in the art.##STR14##

Scheme-8 illustrates the preparation of compounds of Formula Ii fromcompounds of Formula X. The chemistry is analogous to that of Scheme-7.##STR15##

EXAMPLE 1 Preparation of5-Methyl-7-phenyl-2-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine

By the procedure reported by V. A. Lopyrev Zh. Obshch. Khim. 53 p. 1684,1983 (Chemical Abstracts 139865y, 1983) a crude sample of3-amino-5-trifluoromethyl-1,2,4-triazole was prepared by thecyclocondensation of aminoguanidine bicarbonate with trifluoroaceticacid in refluxing toluene. This material was used effectively withoutfurther purification in subsequent ring condensation reactions. To 30ml. of glacial acetic acid stirring, 3.0 g (19.7 mmol) of3-amino-5-trifluoromethyl-1,2,4-triazole and 3.5 g (21.6 mmol) ofbenzoylacetone were added and the mixture heated at reflux for 3 h. Asolution soon formed after heating. The solvent was evaporated in vacuoand excess water added to the residue followed by extraction with 200 mlof ethyl acetate. The extract was washed with water, saturated sodiumbicarbonate, brine, dried over magnesium sulfate and evaporated in vacuoto give an oily residue. Silica gel column chromatography (methylenechloride) afforded 3.09 g of the title compound which was present as themajor component, m.p. 106°-108° C.

A minor regioisomer in which the phenyl and methyl groups on the desiredproduct are reversed was also isolated (240 mg., m.p. 143°-144°) fromthe chromatography.

EXAMPLE 2 Preparation of7-(3-Chlorophenyl)-5-methyl-2-(trifluoromethyl)-1,2,4-triazolo1,5-a]pyrimidine

To 10.0 g (51.0 mmol) of 3'-chloroacetophenone stirring in 100 ml oftetrahydrofuran/100 ml of diethyl ether and 20 ml of ethyl acetate, 4.0g of 50% sodium hydride oil dispersion was added portionwise with acertain amount of foaming. The reaction was stirred at ambienttemperature overnight. Methanol (5.0 ml) was added followed by 150 ml ofwater and 150 ml of diethyl ether. The aqueous layer was separated andacidified with 10% HCl to pH ˜2-3. The aqeuous mixture was re-extractedwith 200 ml of diethyl ether, the ether extract was washed with water(2X), brine, dried over magnesium sulfate, and evaporated in vacuo togive 11.6 g of 3'-chlorobenzoylacetone isolated as an oil. This oil wasused directly in the next step without further purification.

To 5.0 g (32.9 mmol) of 3-amino-5-trifluoromethyl-1,2,4-triazole and 7.0g (36.0 mmol) 3'-chlorobenzoyl-acetone in a round bottom flask, 50 ml ofglacial acetic acid was added and the reaction heated at reflux 3 h. Thesolvent was evaporated in vacuo to give a residue to which excess waterand 200 ml of ethyl acetate was added. The organic layer was separatedand washed with water, saturated sodium bicarbonate, brine, dried overmagnesium sulfate, and evaporated in vacuo to give an oily residue towhich a minimal amount of n-butylchloride was added. On standing, asolid precipitated which was filtered and washed with a small amount ofn-butylchloride to give 2.2 g of the title compound. The filtrate wasconcentrated in vacuo to give an oil which was chromatographed on silicagel (methylene chloride followed by 3:1 ethyl acetate/methylenechloride) to afford another 2.42 g of the title compound, m.p. 115°-116°C.

The minor regio isomer formed in this reaction where the phenyl andmethyl groups are reversed was also isolated from the chromatography ina yield of 690 mg (m.p. 126°-128° C.).

EXAMPLE 3 Preparation of7-Phenyl-2-(trifluoromethyl)1,2,4-triazolo[1.-a]pyrimidine

A mixture of 3.0 ml of acetphenone and 4.0 ml of N,N-dimethylformamidedimethylacetal were heated neat at about 90° for 4 h. After cooling, 4.0g (26.0 mmol) of 3-amino-5-trifluoromethyl-1,2,4-triazole and 70 ml ofglacial acetic acid were added followed by heating at reflux 2 h. Thereaction mixture was evaporated to dryness in vacuo and excess water and200 ml of ethyl acetate added. The ethyl acetate layer was separated,washed with water (2X), saturated sodium bicarbonate, brine, dried overmagnesium sulfate, and evaporated in vacuo to give an oil. Silica gelcolumn chromotagraphy afforded 1.4 g of the title compound (m.p.138°-142° C.). which was the major component present.

EXAMPLE 4 Preparation of5-Methyl-2-(methylthio)-7phenyl-1,2,4-triazolo[1,5-a]pyrimidine

To 50 ml of stirring glacial acetic acid, 2.5 g (19.2 mmol) of3-amino-5-methylthio-1,2,4-triazole and 3.1 g (19.1 mmol) ofbenzoylacetone was added followed by heating at reflux for 2 h. Thesolvent was evaporated in vacuo and excess water added to the residuefollowed by extraction with 200 ml of ethyl acetate. The extract waswashed with water, saturated sodium bicarbonate, brine, dried overmagnesium sulfate and evaporated in vacuo to give an oil. Addition ofn-butyl chloride resulted in crystallization of a solid which wasfiltered and washed with n-butyl chloride to give 1.33 g of the puretitle compound, m.p. 121°-123° C.

EXAMPLE 5 Preparation of5-Methyl-2-(methylsulfonyl)-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

To 2.6 g (10.2 mmol) of5-methyl-2-(methylthio)-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidinestirring in 30 ml of methylene chloride, 4.7 g of 3-chloroperoxy benzoicacid was added portionwise. The mixture was then stirred at ambienttemperature for 45 minutes. Methylene chloride (150 ml) was added andthe solution washed with 10% sodium bisulfite, water, saturated sodiumbicarbonate (2X), brine, dried over magnesium sulfate and evaporated invacuo to give an oily foam. Addition of n-butyl chloride to the foamresulted in crystallization of a solid which was filtered and washedwith the same solvent to give 1.4 g of the title compound, m.p.158°-159° C.

EXAMPLE 6

Preparation of2-Chloro-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

A mixture of 14 g (141.4 mmol) of 3,5-diamino-1,2,4-triazole and 24.0 g(148.1 mmol) benzoylacetone was heated in 200 ml of glacial acetic acidat reflux for 2 hours. A solution soon formed after heating. The solventwas removed in vacuo and the residue dissolved in 400 ml of methylenechloride which was then washed with water (2X), brine and dried overmagnesium sulfate. The solution was concentrated in vacuo (not tocomplete dryness) and ethyl acetate added to the residue. Theprecipitated solid was filtered and washed with ethyl acetate to give16.0 g of reasonably pure intermediate5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-amine which was ableto be taken on directly to the next step without further purificationm.p. 246°-250° .

To 2.0 g (8.9 mmol) of5-methyl-7-phenyl-1,2,4triazolo[1,5-a]pyrimidin-2-amine stirring in 25ml of concentrated hydrochloric acid, 1.2 g (17.4 mmol) of sodiumnitrite dissolved in 4.0 ml of water was added dropwise at ambienttemperature. After the addition, the reaction suspension was warmed atabout 60° for 15 minutes followed by stirring another 10 minutes withoutheat. Ethyl acetate (150 ml) and excess water were added. The ethylacetate layer was separated whereby a certain amount of insolublematerial present was ignored and the extract washed with water (2X),saturated sodium bicarbonate, brine, dried over magnesium sulfate, andevaporated in vacuo to give a solid residue. Silica gel columnchromatography (methylene chloride followed by 10:1 methylenechloride/ethyl acetate) afforded the title compound, m.p. 179°-181° C.

EXAMPLE 7 Preparation of2-Bromo-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine

A mixture of 7.0 g (71 mmol) 3,5-diamino-1,2,4-triazole and 12.0 g (74mmol) benzoylacetone in 100 ml of glacial acetic acid was heated atreflux 2 hours. After cooling, methylene chloride (200 ml) was addedfollowed by the addition of excess water. The organic layer wasseparated, washed with water, brine, dried over magensium sulfate andevaporated in vacuo to give a solid residue to which ethyl acetate wasadded. Filtering gave 16.0 g of crude5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-amine (m.p. 246°-250°C.) which was used directly in the next step.

To 2.0 g (8.9 mmol) of5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-amine stirring in amixture of 20 ml of 48% hydrobromic acid and 10 ml of glacial aceticacid, 2.0 g (29.0 mmol) of sodium nitrite was slowly added portionwisewith good stirring at ambient temperature. The thick suspension wasstirred at about 60° C. for 15 minutes followed by stirring another 10minutes without heat. Ethyl acetate (150 ml) and excess water wereadded. The ethyl acetate layer was separated whereby a certain amount ofinsoluble material present was ignored and the extract washed with water(2X), saturated sodium bicarbonate, brine, dried over magnesium sulfate,and evaporated in vacuo to give a solid residue. Silica gel columnchromatography (methylene chloride followed by 10:1 methylenechloride/ethyl acetate) afforded the title compound, 15 m.p. 178°-180°C.

EXAMPLE 8

Preparation of5-methyl-7-phenyl-2-[(trifluoromethyl)thio]-1,2,4-triazolo[1,5-a]pyrimidine

A mixture of 10.0 9 (86 mmol) 3-amino-5-mercapto-1,2,4-triazole and 14.0g (86.5 mmol) of benzoylacetone in 100 ml of glacial acetic acid washeated at reflux 4 hours. Methylene chloride (500 ml) and excess waterwere added. The organic layer was separated and washed with water,brine, dried over magnesium sulfate and evaporated in vacuo to give aresidue to which n-butyl chloride was added. Filtering gave 4.9 g ofcrude 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol which wasused directly in the next step.

To 1.5 g (6.2 mmol) of5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol and 1.5 g (10.9mmol) of powdered potassium carbonate stirring in 20 ml ofdimethylformamide, 3 ml of condensed trifluoromethyl iodide was addeddropwise at ambient temperature. Keeping the dry ice condenser on fromthe addition, the stirred mixture was warmed to 30° C. At three separatetimes during a 2 h period, 2.0 ml portions of trifluoromethyliodide wereadded. Excess water was added and the aqueous mixture was extracted witha 1:1 mixture of ethyl acetate/diethyl ether (200 ml) and the organiclayer was washed with water, saturated sodium bicarbonate, brine, driedover magnesium sulfate and evaporated in vacuo to give an oil. Silicagel column chromatography (methylene chloride followed by 1:1 methylenechloride/ethyl acetate) afforded 0.4 g of the title compound (maincomponent present), m.p. 91°-93° C.

EXAMPLE 95-methyl-7-(3-trifluoromethylphenyl)-2(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidine

A mixture of 5.5 g (23.9 mmol) of 3'-trifluoromethylbenzoylacetone(prepared by the same procedure as that shown in the beginning ofExample 2 for the preparation of 3'chlorobenzoylacetone) and 3.0 g (19.7mmol) 3-amino-5-trifluoromethyltriazole (prepared as reported inExample 1) were heated at reflux in 50 ml of glacial acetic acid for 2.5h. The solvent was removed in vacuo and the resulting residue dilutedwith excess water and the aqueous mixture extracted with 200 ml of ethylacetate. The extract was washed with water, saturated sodiumbicarbonate, and dried over magnesium sulfate and evaporated in vacuo togive an oily residue.

A solid was triturated on addition of n-butylchloride/hexane and wasfiltered and purified by silica gel column chromatography (methylenechloride) to give 0.7 g of the title compound, m.p. 133°-134° C.

EXAMPLE 10 Preparation of5-methyl-7-phenyl-2-[(2,2,2-trifluoroethoxy]-1,2,4-triazolo[1.5-a]pyrimidine

To 2.5 g (8.7 mmol) of2-bromo-5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine and 4.3 g of2,2,2-trifluoroethanol stirring in 50 ml of THF, 0.4 g of sodium hydride(60% oil dispersion) was added portionwise with considerable foaming.The stirred reaction mixture was heated at reflux 16 hours. Aftercooling, 5.0 ml of methanol of was added followed by the addition of 200ml of ethyl acetate and excess water. The organic layer was washed withwater, brine, dried over magnesium sulfate and evaporated in vacuo togive an oil. Trituration with n-butyl chloride/hexane and filteringafforded 1.4 g of the title compound (m.p. 103°-104° C.).

EXAMPLE 11 Preparation of7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)thiol-1,2,4-triazolo[5-a]pyrimidine

A mixture of 10.0 g (51 mmol) of 3'-chlorobenzoylacetone and 6.0 g (52mmol) of 3-amino-5-mercapto-1,2,4-triazole in 100 ml of glacial aceticacid was heated at reflux 10 hours. The reaction mixture wasconcentrated in vacuo and 500 ml of methylene chloride and excess wateradded. The organic layer was separated and washed with water, brine,dried over magnesium sulfate and evaporated in vacuo to give a solidresidue to which n-butyl chloride was added. Filtration gave 6.2 g ofcrude7-(3-chlorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]-pyrimidin-2-thiolwhich was used directly in the next step.

To 5.6 g (20 mmol) of crude7-(3-chlorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol and2.0 g of potassium hydroxide in 100 ml of dioxane and 30 ml of water,6.0 ml of trifluoromethyl iodide was added by way of a gas additionfunnel equipped with a dry-ice condensor. The mixture was stirred at60°-70° C. (keeping the dry-ice condensor on the reaction) underirradiation from a sunlamp for 2 hours. Ethyl acetate (300 ml) andexcess water were added. The organic layer was separated and washed withwater, brine, dried over magnesium sulfate, and evaporated in vacuo. Theisolated residue was chromatographed on silica gel (3:1 followed by 1:1hexane/ethyl acetate) to afford 2.5 g of the title compound, m.p.95°-96° C.

EXAMPLE 12 Preparation of7-(3-chlorophenyl)-difluoromethyl)-thiol]-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine

To 5.5 g (20.0 mmol) of crude7-(3-chlorophenyl)-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thio 1 and2.7 g of potassium hydroxide stirring in a mixture of 150 ml of dioxaneand 20 ml of water, 8.0 ml of chlorodifluoromethane was added by way ofa gas addition funnel equipped with a dry-ice condensor. The mixture washeated at 60° C. for 1.5 hours. Excess water and a 1:1 mixture of ethylacetate and ethyl ether was added. The organic layer was separated andwashed with water, saturated sodium bicarbonate, brine, dried overmagnesium sulfate, and evaporated in vacuo. The residue waschromatographed on silica gel (methylene chloride followed by 4:1methylene chloride/ethyl acetate) to give 2.5 g of the title compound,m.p. 145°-146° C.

EXAMPLE 13

Preparation of6-methyl-2-(trifluoromethyl)-8-((3-trifluoromethyl)phenyl)-imidazo[1,2-b]pyridazine

A solution of 3 g (12 mmol) of6-methyl-4((3-trifluoromethyl)phenyl)-3-pyridazinamine (prepared from3'-trifluoromethylbenzoylacetone by the method of H. G. O. Becker etal., Tetrahedron. 24, 2687 (1968)) and 2.5 g (13 mmol) of1-bromo-3,3,3-trifluoro-2-propanone in 75 ml of ethanol was refluxed for16 hours. The solvent was removed with a rotary evaporator. The residuewas dissolved in dichloromethane, was washed with saturated aqueoussodium bicarbonate and was dried (sodium sulfate). The solvent wasremoved with a rotary evaporator. The residue was purified by silica gelcolumn chromatography to give 2.04 g of the title compound as a solid,m.p. 122°-123° C.

EXAMPLE 14 Preparation of6-methyl-2-(trifluoromethyl)-8-((3-trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-b]pyridazine

To a slurry of 3.05 9 (13 mmol) of O-diphenylphosphinylhydroxylamine in65 ml of chloroform was added 3.0 g (12 mmol) of6-methyl-4-((3-trifluoromethyl)phenyl-3-pyridazinamine. The mixture wasstirred for 4 hours at room temperature, was refluxed for 2 hours andthen was stirred at room temperature for 16 hours.

The solvent was removed with a rotary evaporator. A 100 ml portion ofwater was added to the residue. The pH was adjusted to 2 with 50% HI.The reaction mixture was filtered and the water was removed from thefiltrate with a rotary evaporator to give 2.5 g of solid.

A 1.4 g portion of this solid was placed in a teflon-capped test tubeand 5 ml of trifluoroacetic anhydride was added. The test tube wasplaced in an oil bath heated to 200° C. for 15 minutes. After cooling,the residue was dissolved in dichloromethane and was washed with asaturated aqueous sodium bicarbonate solution and was dried (sodiumsulfate). The solvent was removed with a rotary evaporator. The residuewas purified by silica gel column chromatography to give 0.74 g of thetitle compound as a solid, m.p. 134°-135.5° C.

EXAMPLE 15 Preparation of5-methyl-7-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-carbonitrile

To a solution of 30 g (0.17 mole) of1,1-dicyano-2-chloro-2-trifluoromethylethylene (prepared as taught by V.I. Krokhtyak et al., J. Org. Chem. (U.S.S.R), 1441 (1981)) in 300 ml ofether at 0° C. was added 10.6 ml (0.33 mole) of hydrazine dropwise. Thereaction waas stirred 30 minutes at room temperature. It was filteredand the solvent was removed with a rotary evaporator to give 28 g of ayellow semi-solid.

A 5.4 g (30 mmol) sample of this material was dissolved in 90 ml ofethanol and 5.0 g (30 mmol) of benzoylacetone was added. The reactionmixture was heated at reflux for 16 hours. It was cooled and the solventwas removed with a rotary evaporator. The residue was purified by silicagel column chromotography to give 4.7 g of the title compound as asolid, m.p. 143°-148° C.

Using the procedures outlined in Schemes 1-8 and Examples 1-15, thecompounds of Tables I-VIII can be prepared.

                  TABLE I                                                         ______________________________________                                         ##STR16##                                                                    R.sub.1   R.sub.2      R.sub.4 R.sub.5  R.sub.6                               ______________________________________                                        Me        CF.sub.3     H       CF.sub.3 H                                     Me        CH.sub.3     H       Cl       H                                     Me        CF.sub.3     H       Br       H                                     Me        CF.sub.3     H       CN       H                                     Me        CF.sub.3     H       OCF.sub.3                                                                              H                                     Me        CF.sub.3     H       OCHF.sub.2                                                                             H                                     Me        CF.sub.3     H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        CF.sub.3     H       SCF.sub.3                                                                              H                                     Me        CF.sub.3     H       SCHF.sub.2                                                                             H                                     Me        CF.sub.3     H       SO.sub.2 CF.sub.3                                                                      H                                     Me        CF.sub.3     H       H        H                                     Me        CF.sub.3     H       OMe      H                                     Me        CF.sub.3     H       OEt      H                                     Me        CF.sub.3     H       Me       H                                     Me        CF.sub.3     H       C.sub.2 F.sub.5                                                                        H                                     Et        CF.sub.3     H       CF.sub.3 H                                     Et        CH.sub.3     H       Cl       H                                     Et        CF.sub.3     H       Br       H                                     Et        CF.sub.3     H       CN       H                                     Et        CF.sub.3     H       OCF.sub.3                                                                              H                                     Et        CF.sub.3     H       OCHF.sub.2                                                                             H                                     Et        CF.sub.3     H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        CF.sub.3     H       SCF.sub.3                                                                              H                                     Et        CF.sub.3     H       SCHF.sub.2                                                                             H                                     Et        CF.sub.3     H       SO.sub.2 CF.sub.3                                                                      H                                     Et        CF.sub.3     H       H        H                                     Et        CF.sub.3     H       SO.sub.2 CHF.sub.2                                                                     H                                     Et        CF.sub.3     H       SC.sub.2 F.sub.5                                                                       H                                     Et        CF.sub.3     H       SO.sub.2 C.sub.2 F.sub.5                                                               H                                     Et        CF.sub.3     H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        CF.sub.3     H       CF.sub.3 H                                     Pr        CH.sub.3     H       Cl       H                                     Pr        CF.sub.3     H       Br       H                                     Pr        CF.sub.3     H       CN       H                                     Pr        CF.sub.3     H       OCF.sub.3                                                                              H                                     Pr        CF.sub.3     H       OCHF.sub.2                                                                             H                                     Pr        CF.sub.3     H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        CF.sub.3     H       SCF.sub.3                                                                              H                                     Pr        CF.sub.3     H       SCHF.sub.2                                                                             H                                     Pr        CF.sub.3     H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        CF.sub.3     H       OH       H                                     Pr        CF.sub.3     H       CONH.sub.2                                                                             H                                     Et        CF.sub.3     H       NHSO.sub.2 CF.sub.3                                                                    H                                     Me        CHF.sub.2    H       CF.sub.3 H                                     Me        CHF.sub.2    H       Cl       H                                     Me        CHF.sub.2    H       Br       H                                     Me        CHF.sub.2    H       CN       H                                     Me        CHF.sub.2    H       OCF.sub.3                                                                              H                                     Me        CHF.sub.2    H       OCHF.sub.2                                                                             H                                     Me        CHF.sub.2    H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        CHF.sub.2    H       SCF.sub.3                                                                              H                                     Me        CHF.sub.2    H       SCHF.sub.2                                                                             H                                     Me        CHF.sub.2    H       SO.sub.2 CF.sub.3                                                                      H                                     Me        CHF.sub.2    H       H        H                                     Et        CHF.sub.2    H       CF.sub.3 H                                     Et        CHF.sub.2    H       Cl       H                                     Et        CHF.sub.2    H       Br       H                                     Et        CHF.sub.2    H       CN       H                                     Et        CHF.sub.2    H       OCF.sub.3                                                                              H                                     Et        CHF.sub.2    H       OCHF.sub.2                                                                             H                                     Et        CHF.sub.2    H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        CHF.sub.2    H       SCF.sub.3                                                                              H                                     Et        CHF.sub.2    H       SCHF.sub.2                                                                             H                                     Et        CHF.sub.2    H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        CHF.sub.2    H       CF.sub.3 H                                     Pr        CHF.sub.2    H       Cl       H                                     Pr        CHF.sub.2    H       Br       H                                     Pr        CHF.sub.2    H       CN       H                                     Pr        CHF.sub.2    H       OCF.sub.3                                                                              H                                     Pr        CHF.sub.2    H       OCHF.sub.2                                                                             H                                     Pr        CHF.sub.2    H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        CHF.sub.2    H       SCF.sub.3                                                                              H                                     Pr        CHF.sub.2    H       SCHF.sub.2                                                                             H                                     Pr        CHF.sub.2    H       SO.sub.2 CF.sub.3                                                                      H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       CF.sub.3 H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       Cl       H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       Br       H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       CN       H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       OCF.sub.3                                                                              H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       OCHF.sub.2                                                                             H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       SCF.sub.3                                                                              H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       SCHF.sub.2                                                                             H                                     Me        OCH.sub.2 CF.sub.3                                                                         H       SO.sub.2 CF.sub.3                                                                      H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       CF.sub.3 H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       Cl       H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       Br       H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       CN       H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       OCF.sub.3                                                                              H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       OCHF.sub.2                                                                             H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       SCF.sub.3                                                                              H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       SCHF.sub.2                                                                             H                                     Et        OCH.sub.2 CF.sub.3                                                                         H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       CF.sub.3 H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       Cl       H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       Br       H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       CN       H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       OCF.sub.3                                                                              H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       OCHF.sub.2                                                                             H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       SCF.sub.3                                                                              H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       SCHF.sub.2                                                                             H                                     Pr        OCH.sub.2 CF.sub.3                                                                         H       SO.sub.2 CF.sub.3                                                                      H                                     Me        OCHF.sub.2   H       CF.sub.3 H                                     Me        OCHF.sub.2   H       Cl       H                                     Me        OCHF.sub.2   H       Br       H                                     Me        OCHF.sub.2   H       CN       H                                     Me        OCHF.sub.2   H       OCF.sub.3                                                                              H                                     Me        OCHF.sub.2   H       OCHF.sub.2                                                                             H                                     Me        OCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        OCHF.sub.2   H       SCF.sub.3                                                                              H                                     Me        OCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Me        OCHF.sub.2   H       SO.sub.2 CF.sub.3                                                                      H                                     Et        OCHF.sub.2   H       CF.sub.3 H                                     Et        OCHF.sub.2   H       Cl       H                                     Et        OCHF.sub.2   H       Br       H                                     Et        OCHF.sub.2   H       CN       H                                     Et        OCHF.sub.2   H       OCF.sub.3                                                                              H                                     Et        OCHF.sub.2   H       OCHF.sub. 2                                                                            H                                     Et        OCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        OCHF.sub.2   H       SCF.sub.3                                                                              H                                     Et        OCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Et        OCHF.sub.2   H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        OCHF.sub.2   H       CF.sub.3 H                                     Pr        OCHF.sub.2   H       Cl       H                                     Pr        OCHF.sub.2   H       Br       H                                     Pr        OCHF.sub.2   H       CN       H                                     Pr        OCHF.sub.2   H       OCF.sub.3                                                                              H                                     Pr        OCHF.sub.2   H       OCHF.sub.2                                                                             H                                     Pr        OCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        OCHF.sub.2   H       SCF.sub.3                                                                              H                                     Pr        OCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Pr        OCHF.sub.2   H       SO.sub.2 CF.sub.3                                                                      H                                     Me        OCF.sub.3    H       CF.sub.3 H                                     Me        OCF.sub.3    H       Cl       H                                     Me        OCF.sub.3    H       Br       H                                     Me        OCF.sub.3    H       CN       H                                     Me        OCF.sub.3    H       OCF.sub.3                                                                              H                                     Me        OCF.sub.3    H       OCHF.sub.2                                                                             H                                     Me        OCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        OCF.sub.3    H       SCF.sub.3                                                                              H                                     Me        OCF.sub.3    H       SCHF.sub.2                                                                             H                                     Me        OCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Et        OCF.sub.3    H       CF.sub.3 H                                     Et        OCF.sub.3    H       Cl       H                                     Et        OCF.sub.3    H       Br       H                                     Et        OCF.sub.3    H       CN       H                                     Et        OCF.sub.3    H       OCF.sub.3                                                                              H                                     Et        OCF.sub.3    H       OCHF.sub.2                                                                             H                                     Et        OCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        OCF.sub.3    H       SCF.sub.3                                                                              H                                     Et        OCF.sub.3    H       SCHF.sub.2                                                                             H                                     Et        OCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        OCF.sub.3    H       CF.sub.3 H                                     Pr        OCF.sub.3    H       Cl       H                                     Pr        OCF.sub.3    H       Br       H                                     Pr        OCF.sub.3    H       CN       H                                     Pr        OCF.sub.3    H       OCF.sub.3                                                                              H                                     Pr        OCF.sub.3    H       OCHF.sub.2                                                                             H                                     Pr        OCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        OCF.sub.3    H       SCF.sub.3                                                                              H                                     Pr        OCF.sub.3    H       SCHF.sub.2                                                                             H                                     Pr        OCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Me        SCF.sub.3    H       CF.sub.3 H                                     Me        SCF.sub.3    H       Cl       H                                     Me        SCF.sub.3    H       Br       H                                     Me        SCF.sub.3    H       CN       H                                     Me        SCF.sub.3    H       OCF.sub.3                                                                              H                                     Me        SCF.sub.3    H       OCHF.sub.2                                                                             H                                     Me        SCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        SCF.sub.3    H       SCF.sub.3                                                                              H                                     Me        SCF.sub.3    H       SCHF.sub.2                                                                             H                                     Me        SCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Et        SCF.sub.3    H       CF.sub.3 H                                     Et        SCF.sub.3    H       Cl       H                                     Et        SCF.sub.3    H       Br       H                                     Et        SCF.sub.3    H       CN       H                                     Et        SCF.sub.3    H       OCF.sub.3                                                                              H                                     Et        SCF.sub.3    H       OCHF.sub.2                                                                             H                                     Et        SCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        SCF.sub.3    H       SCF.sub.3                                                                              H                                     Et        SCF.sub.3    H       SCHF.sub.2                                                                             H                                     Et        SCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        SCF.sub.3    H       CF.sub.3 H                                     Pr        SCF.sub.3    H       Cl       H                                     Pr        SCF.sub.3    H       Br       H                                     Pr        SCF.sub.3    H       CN       H                                     Pr        SCF.sub.3    H       OCF.sub.3                                                                              H                                     Pr        SCF.sub.3    H       OCHF.sub.2                                                                             H                                     Pr        SCF.sub.3    H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        SCF.sub.3    H       SCF.sub.3                                                                              H                                     Pr        SCF.sub.3    H       SCHF.sub.2                                                                             H                                     Pr        SCF.sub.3    H       SO.sub.2 CF.sub.3                                                                      H                                     Me        SCHF.sub.2   H       CF.sub.3 H                                     Me        SCHF.sub.2   H       Cl       H                                     Me        SCHF.sub.2   H       Br       H                                     Me        SCHF.sub.2   H       CN       H                                     Me        SCHF.sub.2   H       OCF.sub.3                                                                              H                                     Me        SCHF.sub.2   H       OCHF.sub.2                                                                             H                                     Me        SCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Me        SCHF.sub.2   H       SCF.sub.3                                                                              H                                     Me        SCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Me        SCHF.sub.2   H       SO.sub.2 CF.sub. 3                                                                     H                                     Et        SCHF.sub.2   H       CF.sub.3 H                                     Et        SCHF.sub.2   H       Cl       H                                     Et        SCHF.sub.2   H       Br       H                                     Et        SCHF.sub.2   H       CN       H                                     Et        SCHF.sub.2   H       OCF.sub.3                                                                              H                                     Et        SCHF.sub.2   H       OCHF.sub.2                                                                             H                                     Et        SCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Et        SCHF.sub.2   H       SCF.sub.3                                                                              H                                     Et        SCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Et        SCHF.sub.2   H       SO.sub.2 CF.sub.3                                                                      H                                     Pr        SCHF.sub.2   H       CF.sub.3 H                                     Pr        SCHF.sub.2   H       Cl       H                                     Pr        SCHF.sub.2   H       Br       H                                     Pr        SCHF.sub.2   H       CN       H                                     Pr        SCHF.sub.2   H       OCF.sub.3                                                                              H                                     Pr        SCHF.sub.2   H       OCHF.sub.2                                                                             H                                     Pr        SCHF.sub.2   H       OCH.sub.2 CF.sub.3                                                                     H                                     Pr        SCHF.sub.2   H       SCF.sub.3                                                                              H                                     Pr        SCHF.sub.2   H       SCHF.sub.2                                                                             H                                     Pr        SCHF.sub.2   H       SO.sub.2 CF.sub.3                                                                      H                                     Me        SMe          H       H        H                                     Me        SMe          H       CN       H                                     Et        SMe          H       CF.sub.3 H                                     Pr        SMe          H       CF.sub.3 H                                     Pr        SMe          H       Cl       H                                     Me        SO.sub.2 Me  H       H        H                                     Pr        SO.sub.2 Me  H       CF.sub.3 H                                     Me        Cl           H       H        H                                     Me        Cl           H       CF.sub.3 H                                     Me        Cl           H       CF.sub.3 H                                     Me        Br           H       Br       H                                     Me        Br           H       CF.sub.3 H                                     Me        Br           H       OCF.sub.3                                                                              H                                     Et        Br           H       CF.sub.3 H                                     Et        Br           H       Cl       H                                     Et        Br           H       Br       H                                     Pr        Br           H       CF.sub.3 H                                     Me        SO.sub.2 CF.sub.3                                                                          H       H        H                                     Me        SO.sub.2 CF.sub.3                                                                          H       CF.sub.3 H                                     Et        SO.sub.2 CF.sub.3                                                                          H       Cl       H                                     Me        CCl.sub.3    H       H        H                                     Me        CCl.sub.3    H       Cl       H                                     Me        CCl.sub.3    H       CF.sub.3 H                                     Et        CCl.sub.3    H       Cl       H                                     Me        OCH(CH.sub.3)CF.sub.3                                                                      H       CF.sub.3 H                                     Me        OCH(CH.sub.3)CF.sub.3                                                                      H       Cl       H                                     Me        CF.sub.2 Cl  H       CF.sub.3 H                                     Me        CF.sub.2 Cl  H       Cl       H                                     H         CF.sub.3     H       H        H                                     H         CF.sub.3     H       Cl       H                                     H         Cl           H       CF.sub.3 H                                     i-Pr      CF.sub.3     H       Cl       H                                     i-Pr      CF.sub.3     H       CF.sub.3 H                                     n-Bu      CF.sub.3     H       Cl       H                                     n-Bu      CF.sub.3     H       CF.sub.3 H                                     FCH.sub.2 CF.sub.3     H       CF.sub.3 H                                     C.sub.2 CH                                                                              CF.sub.3     H       CF.sub.3 H                                     ClCH.sub.2                                                                              CF.sub.3     H       Cl       H                                     MeS       CF.sub.3     H       Br       H                                     MeS       CF.sub. 3    H       CF.sub.3 H                                     EtS       CF.sub.3     H       CF.sub.3 H                                     MeO       CF.sub.3     H       Cl       H                                     MeO       CF.sub.3     H       CF.sub.3 H                                     EtO       CF.sub.3     H       CF.sub.3 H                                     EtO       CF.sub.3     H       Br       H                                     MeNH      CF.sub.3     H       CF.sub.3 H                                     Me.sub.2 N                                                                              CF.sub.3     H       Br       H                                     CH.sub.3 CO                                                                             CF.sub.3     H       Br       H                                     CH.sub.3 CO                                                                             CF.sub.3     H       Cl       H                                     CH.sub.3 CO                                                                             CF.sub.3     H       CF.sub.3 H                                     MeOCH.sub.2                                                                             CF.sub.3     H       Cl       H                                     EtOCH.sub.2                                                                             CF.sub.3     H       CF.sub.3 H                                     F.sub.2 CHO                                                                             CF.sub.3     H       Cl       H                                     FCH.sub.2 CH.sub.2 O                                                                    CF.sub.3     H       Cl       H                                     CH.sub.3 CH.sub.2 CHCl                                                                  SCH.sub.3    H       CF.sub.3 H                                     CH.sub.2CH                                                                              CF.sub.3     H       CF.sub.3 H                                     CH.sub.2CH                                                                              CF.sub.3     H       Cl       H                                     CH.sub.2CH                                                                              CHF.sub.2    H       Br       H                                     CH.sub.2CH                                                                              OCF.sub.3    H       CF.sub.3 H                                     CH.sub.2CH                                                                              OCHF.sub.2   H       SCF.sub.3                                                                              H                                     CH.sub.2CH                                                                              OCH.sub.2 CF.sub.3                                                                         H       OCF.sub.3                                                                              H                                     CH.sub.2CH                                                                              SCF.sub.3    H       CN       H                                     CHC       CF.sub.3     H       CF.sub.3 H                                     CHC       CHF.sub.2    H       Cl       H                                     CHC       OCF.sub.3    H       CN       H                                     CHC       OCHF.sub.2   H       OCF.sub.3                                                                              H                                     CHC       OCH.sub.2 CF.sub.3                                                                         H       Br       H                                     CHC       SCF.sub.3    H       SCF.sub.3                                                                              H                                     CHC       SCHF.sub.2   H       OCHF.sub.2                                                                             H                                     CH.sub.3 CHCH                                                                           CF.sub.3     H       Cl       H                                     CH.sub.3 CHCH                                                                           CF.sub.3     H       CN       H                                     CH.sub.3 CHCH                                                                           SCF.sub.3    H       Br       H                                     CH.sub.3 CHCH                                                                           CHF.sub.2    H       OCF.sub.3                                                                              H                                     CH.sub.3 CHCH                                                                           OCF.sub.3    H       SCF.sub.3                                                                              H                                     CH.sub.3 CHCH                                                                           OCH.sub.2 CF.sub.3                                                                         H       SCHF.sub.2                                                                             H                                     Me        CF.sub.3     H       4-Cl     H                                     Me        CF.sub.3     H       2-Cl     H                                     Me        CF.sub.3     H       4-OMe    H                                     Me        CF.sub.3     H       2-Me     H                                     Me        CF.sub.3     H       2-F      H                                     Me        CF.sub.3     H       4-F      H                                     Me        CF.sub.3     OMe     5-OMe    H                                     Me        CF.sub.3     OMe     2-OMe    H                                     Me        CF.sub.3     Me      4-Me     H                                     Me        CF.sub.3     Cl      5-Cl     H                                     Me        CF.sub.3     Cl      2-Cl     H                                     Me        CF.sub.3     Cl      5-OMe    H                                     Me        CF.sub.3     F       5-F      H                                     Me        CF.sub.3     Cl      2-OMe    H                                     Me        CF.sub.3     CF.sub.3                                                                              5-F      H                                     Et        CF.sub.3     Cl      5-Cl     H                                     ______________________________________                                    

                  TABLE II                                                        ______________________________________                                         ##STR17##                                                                    R.sub.1 R.sub.2    R.sub.4                                                                              R.sub.5  R.sub.6                                                                            R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   CF.sub.3                                                                             H        H    H                                     H       CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SMe        Cl     H        H    H                                     Me      Cl         CF.sub.3                                                                             H        H    H                                     Me      SEt        CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   Cl     H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        F    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Br                                    Et      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    F                                     Et      CF.sub.3   Cl     H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-CN     H    H                                     MeO     CF.sub.3   CF.sub.3                                                                             H        H    H                                     F.sub.2 CH                                                                            CF.sub.3   Cl     H        H    H                                     Et      SMe        OMe    H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         OMe    H        H    H                                     Me      CF.sub.3   Cl     H        F    H                                     isopropyl                                                                             CF.sub.3   Cl     H        H    H                                     MeS     CF.sub.3   Cl     H        H    H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl     H        H    H                                     Me      CF.sub.3   H      3-SO.sub.2 CF.sub.3                                                                    H    H                                     Me      CF.sub.3   H      3-SO.sub.2 Me                                                                          H    H                                     Et      Br         Cl     H        H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    Cl                                    Me      CF.sub.3   Cl     H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Et      CF.sub.3   H      3-OCHF.sub.2                                                                           H    H                                     Me      CF.sub.3   H      3-OCHF.sub.2                                                                           H    CN                                    n-propyl                                                                              CF.sub.3   H      3-OCF.sub.3                                                                            H    CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Et      Br         CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   OMe    H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Me                                    Et      CF.sub.3   Cl     H        H    CO.sub.2 Me                           Me      CF.sub.3   H      3-OCH.sub.2 CF.sub.3                                                                   H    CN                                    Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    CN                                    Et      CF.sub.3   H      3-SCHF.sub.2                                                                           H    CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    Cl                                    ET      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-CN     H    CN                                    n-propyl                                                                              CF.sub.3   H      3-CN     H    CN                                    Et      CF.sub.3   H      3-SMe    H    CN                                    Et      Cl         H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Br     H        H    CN                                    HCC     CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-SO.sub.2 CHF.sub.2                                                                   H    CN                                    Me      CF.sub.3   Cl     3-Cl     H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                             H        H    CN                                    Et      CHF.sub.2  CF.sub.3                                                                             H        H    CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      OCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H      H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CONH.sub.2                            Me      CF.sub.3   Cl     H        H    CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                             H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        H    CO.sub.2 Et                           Me      CF.sub.3   Cl     H        H    CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    H                                     Me      OCF.sub.2 H                                                                              Cl     H        H    CN                                    Me      OCF.sub.2 H                                                                              Cl     H        H    H                                     Me      OCF.sub.3  CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.3  CF.sub.3                                                                             H        H    H                                     ______________________________________                                    

                  TABLE III                                                       ______________________________________                                         ##STR18##                                                                    R.sub.1 R.sub.2    R.sub.4                                                                              R.sub.5  R.sub.6                                                                            R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   CF.sub.3                                                                             H        H    H                                     H       CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SMe        Cl     H        H    H                                     Me      Cl         CF.sub.3                                                                             H        H    H                                     Me      SEt        CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   Cl     H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        F    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Br                                    Et      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    F                                     Et      CF.sub.3   Cl     H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-CN     H    H                                     MeO     CF.sub.3   CF.sub.3                                                                             H        H    H                                     F.sub.2 CH                                                                            CF.sub.3   Cl     H        H    H                                     Et      SMe        OMe    H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         OMe    H        H    H                                     Me      CF.sub.3   Cl     H        F    H                                     isopropyl                                                                             CF.sub.3   Cl     H        H    H                                     MeS     CF.sub.3   Cl     H        H    H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl     H        H    H                                     Me      CF.sub.3   H      3-SO.sub.2 CF.sub.3                                                                    H    H                                     Me      CF.sub.3   H      3-SO.sub.2 Me                                                                          H    H                                     Et      Br         Cl     H        H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    Cl                                    Me      CF.sub.3   Cl     H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    N                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Et      CF.sub.3   H      3-OCHF.sub.2                                                                           H    H                                     Me      CF.sub.3   H      3-OCHF.sub.2                                                                           H    CN                                    n-propyl                                                                              CF.sub.3   H      3-OCF.sub.3                                                                            H    CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Et      Br         CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   OMe    H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Me                                    Et      CF.sub.3   Cl     H        H    CO.sub.2 Me                           Me      CF.sub.3   H      3-OCH.sub.2 CF.sub.3                                                                   H    CN                                    Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    CN                                    Et      CF.sub.3   H      3-SCHF.sub.2                                                                           H    CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    Cl                                    Et      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-CN     H    CN                                    n-propyl                                                                              CF.sub.3   H      3-CN     H    CN                                    Et      CF.sub.3   H      3-SMe    H    CN                                    Et      Cl         H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Br     H        H    CN                                    HCC     CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-SO.sub.2 CHF.sub.2                                                                   H    CN                                    Me      CF.sub.3   Cl     3-Cl     H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                             H        H    CN                                    Et      CHF.sub.2  CF.sub.3                                                                             H        H    CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      OCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H      H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CONH.sub.2                            Me      CF.sub.3   Cl     H        H    CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                             H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        H    CO.sub.2 Et                           Me      CF.sub.3   Cl     H        H    CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    H                                     Me      OCF.sub.2 H                                                                              Cl     H        H    CN                                    Me      OCF.sub.2 H                                                                              Cl     H        H    H                                     Me      OCF.sub.3  CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.3  CF.sub.3                                                                             H        H    H                                     ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                         ##STR19##                                                                    R.sub.1 R.sub.2    R.sub.4                                                                              R.sub.5   R.sub.6                                                                           R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                             H         H   H                                     Me      CF.sub.3   Cl     H         H   H                                     Et      CF.sub.3   Cl     H         H   H                                     Et      CF.sub.3   CF.sub.3                                                                             H         H   H                                     H       CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      SMe        Cl     H         H   H                                     Me      Cl         CF.sub.3                                                                             H         H   H                                     Me      SEt        CF.sub.3                                                                             H         H   H                                     Me      CF.sub.3   H      3-SCF.sub.3                                                                             H   H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H         H   CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H         H   H                                     Me      CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      CF.sub.3   Cl     H         H   CN                                    Me      CF.sub.3   CF.sub.3                                                                             H         F   CN                                    Me      CF.sub.3   CF.sub.3                                                                             H         H   Br                                    Et      CF.sub.3   CF.sub.3                                                                             H         H   CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      CF.sub.3   CF.sub.3                                                                             H         H   F                                     Et      CF.sub.3   Cl     H         H   CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H         H   H                                     Me      CF.sub.3   H      3-CN      H   H                                     MeO     CF.sub.3   CF.sub.3                                                                             H         H   H                                     F.sub.2 CH                                                                            CF.sub.3   Cl     H         H   H                                     Et      SMe        OMe    H         H   H                                     Me      CF.sub.3   CF.sub.3                                                                             H         F   H                                     Me      Cl         OMe    H         H   H                                     Me      CF.sub.3   Cl     H         F   H                                     isopropyl                                                                             CF.sub.3   Cl     H         H   H                                     MeS     CF.sub.3   Cl     H         H   H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl     H         H   H                                     Me      CF.sub.3   H      3-SO.sub.2 CF.sub.3                                                                     H   H                                     Me      CF.sub.3   H      3-SO.sub.2 Me                                                                           H   H                                     Et      Br         Cl     H         H   H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H         H   Cl                                    Me      CF.sub.3   Cl     H         H   NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H         F   H                                     Me      Cl         CF.sub.3                                                                             H         H   CN                                    Et      Cl         CF.sub.3                                                                             H         H   CN                                    Et      Cl         CF.sub.3                                                                             H         H   N                                     Me      SCHF.sub.2 CF.sub.3                                                                             H         H   H                                     Et      CF.sub.3   H      3-CN      H   H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H         H   CN                                    Et      CF.sub.3   H      3-OCHF.sub.2                                                                            H   H                                     Me      CF.sub.3   H      3-OCHF.sub.2                                                                            H   CN                                    n-propyl                                                                              CF.sub.3   H      3-OCF.sub.3                                                                             H   CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Et      Br         CF.sub.3                                                                             H         H   H                                     Et      CF.sub.3   OMe    H         H   CN                                    Me      CF.sub.3   CF.sub.3                                                                             H         H   Me                                    Et      CF.sub.3   Cl     H         H   CO.sub.2 Me                           Me      CF.sub.3   H      3-OCH.sub.2 CF.sub.3                                                                    H   CN                                    Me      CF.sub.3   H      3-SCF.sub.3                                                                             H   CN                                    Et      CF.sub.3   H      3-SCHF.sub.2                                                                            H   CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      Cl         CF.sub.3                                                                             H         H   Cl                                    Et      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                             H         H   CN                                    Me      Cl         CF.sub.3                                                                             H         H   CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                             H         H   CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                             H         H   CN                                    Me      CF.sub.3   H      3-CN      H   CN                                    n-propyl                                                                              CF.sub.3   H      3-CN      H   CN                                    Et      CF.sub.3   H      3-SMe     H   CN                                    Et      Cl         H      3-CN      H   H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H         H   H                                     Me      CF.sub.3   Br     H         H   CN                                    HCC     CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      CF.sub.3   H      3-SO.sub.2 CHF.sub.2                                                                    H   CN                                    Me      CF.sub.3   Cl     3-Cl      H   CN                                    Me      CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                             H         H   CN                                    Et      CHF.sub.2  CF.sub.3                                                                             H         H   CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                             H         H   CN                                    Me      OCHF.sub.2 CF.sub.3                                                                             H         H   CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H      H         H   H                                     Me      CF.sub.3   CF.sub.3                                                                             H         H   CONH.sub.2                            Me      CF.sub.3   Cl     H         H   CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                             H         H   NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H         H   CO.sub.2 Et                           Me      CF.sub.3   Cl     H         H   CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H         H   CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H         H   H                                     Me      OCF.sub.2 H                                                                              Cl     H         H   CN                                    Me      OCF.sub.2 H                                                                              Cl     H         H   H                                     Me      OCF.sub.3  CF.sub.3                                                                             H         H   CN                                    Me      OCF.sub.3  CF.sub.3                                                                             H         H   H                                     ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR20##                                                                    R.sub.1   R.sub.2      R.sub.4                                                                              R.sub.5    R.sub.6                              ______________________________________                                        Me        CF.sub.3     H      H          H                                    Me        SMe          H      H          H                                    Me        SO.sub.2 Me  H      H          H                                    Me        Cl           H      H          H                                    Me        Br           H      H          H                                    Me        SCF.sub.3    H      H          H                                    H         CF.sub.3     H      H          H                                    Me        SO.sub.2 CF.sub.3                                                                          H      H          H                                    Me        CCl.sub.3    H      H          H                                    Me        CF.sub.3     H      4-Cl       H                                    Me        CF.sub.3     OMe    H          H                                    Me        OCH.sub.2 CF.sub.3                                                                         CF.sub.3                                                                             H          H                                    Me        OCH.sub.2 CHF.sub.2                                                                        CF.sub.3                                                                             H          H                                    Me        OCH.sub.2 CF.sub.3                                                                         Cl     H          H                                    Me        OCH(CH.sub.3)CF.sub.3                                                                      CF.sub.3                                                                             H          H                                    Et        OCH.sub.2 CF.sub.3                                                                         CF.sub.3                                                                             H          H                                    n-propyl  OCH.sub.2 CF.sub. 3                                                                        CF.sub.3                                                                             H          H                                    Et        OCH.sub.2 CF.sub.3                                                                         Cl     H          H                                    MeSCH.sub.2                                                                             CF.sub.3     CF.sub.3                                                                             H          H                                    Me        OCH.sub.2 CF.sub.3                                                                         H      3-CN       H                                    Me        CF.sub.3     H      2-Cl       H                                    Et        CF.sub.3     H      H          H                                    Me        CF.sub.3     F      H          H                                    Me        CF.sub.3     Cl     H          H                                    Me        CF.sub.3     H      4-OMe      H                                    Me        CF.sub.3     Me     H          H                                    Me        CF.sub.3     CF.sub.3                                                                             H          H                                    Me        CF.sub.3     H      2-Me       H                                    Me        CF.sub.3     Br     H          H                                    Me        CF.sub.3     OMe    5-OMe      H                                    Me        CF.sub.3     OMe    2-OMe      H                                    Me        CF.sub.3     Me     4-Me       H                                    Me        OCH.sub.2 CF.sub.3                                                                         H      H          H                                    Me        CF.sub.3     H      3-SMe      H                                    Me        CF.sub.3     H      3-SO.sub.2 Me                                                                            H                                    Me        CF.sub.3     H      3-SCF.sub.3                                                                              H                                    Me        CF.sub.3     H      3-SO.sub.2 CF.sub.3                                                                      H                                    Me        CF.sub.3     OEt    H          H                                    Me        CF.sub.3     H      3-Ph       H                                    Me        CF.sub.3     H      3-OPh      H                                    Me        CF.sub.3     H      3-CO.sub.2 Me                                                                            H                                    Me        CF.sub.3     H      3-OCHF.sub.2                                                                             H                                    Me        CF.sub.3     H      3-CN       H                                    Me        CF.sub.3     H      3-CH.sub.2 Br                                                                            H                                    Me        CF.sub.3     H      3-n-propyl H                                    Me        CF.sub.3     H      3-isopropyl                                                                              H                                    Me        CF.sub.3     H      3-SEt      H                                    Me        CF.sub.3     H      3-OCH.sub.2 CF.sub.3                                                                     H                                    Me        CF.sub.3     Cl     3-Cl       H                                    Me        OCF.sub.3    CF.sub.3                                                                             H          H                                    Me        OCF.sub.3    Cl     H          H                                    Me        OCHF.sub.2   H      3-CN       H                                    Me        SCHF.sub.2   H      3-CN       H                                    Me        CF.sub.3     H      3-OCF.sub.2 CF.sub.3                                                                     H                                    Me        CF.sub.3     H      3-OCF.sub.3                                                                              H                                    Me        CF.sub.3     H      3-NO.sub.2 H                                    Me        SEt          Cl     H          H                                    Me        Cl           CF.sub.3                                                                             H          H                                    Me        Cl           H      3-SMe      H                                    Me        Br           CF.sub.3                                                                             H          H                                    Me        SCF.sub.3    CF.sub.3                                                                             H          H                                    Me        SCF.sub.3    Cl     H          H                                    Me        SO.sub.2 CF.sub.3                                                                          CF.sub.3                                                                             H          H                                    Me        CCl.sub.3    Cl     H          H                                    Me        OCHF.sub.2   Cl     H          H                                    H         CF.sub.3     Cl     H          H                                    Me        CF.sub.3     H      3-CH.sub.2 OMe                                                                           H                                    Me        CF.sub.3     H      3-COCH.sub.3                                                                             H                                    H         Cl           CF.sub.3                                                                             H          H                                    Et        CF.sub.3     CF.sub.3                                                                             H          H                                    Et        CCl.sub.3    Cl     H          H                                    Et        CF.sub.3     Cl     H          H                                    Et        SCF.sub.3    CF.sub.3                                                                             H          H                                    Et        SCF.sub.3    Cl     H          H                                    Et        SO.sub.2 CF.sub.3                                                                          Cl     H          H                                    n-propyl  CF.sub.3     CF.sub.3                                                                             H          H                                    isopropyl CF.sub. 3    Cl     H          H                                    n-butyl   CF.sub.3     CF.sub.3                                                                             H          H                                    FCH.sub.2 CF.sub.3     CF.sub.3                                                                             H          H                                    F.sub.2 CH                                                                              CF.sub.3     Cl     H          H                                    ClCH.sub.2                                                                              CF.sub.3     Cl     H          H                                    MeO       CF.sub.3     Cl     H          H                                    EtO       CF.sub.3     CF.sub.3                                                                             H          H                                    Me        OCHF.sub.2   CF.sub.3                                                                             H          H                                    Me        SCHF.sub.2   CF.sub.3                                                                             H          H                                    Me        SCHF.sub.2   Cl     H          H                                    Me        CHF.sub.2    CF.sub.3                                                                             H          H                                    Me        CF.sub.2 Cl  CF.sub.3                                                                             H          H                                    Me        CF.sub.2 Cl  Cl     H          H                                    MeOCH.sub.2                                                                             CF.sub.3     Cl     H          H                                    EtOCH.sub.2                                                                             CF.sub.3     CF.sub.3                                                                             H          H                                    F.sub.2 CHO                                                                             CF.sub.3     Cl     H          H                                    FCH.sub.2 O                                                                             CF.sub.3     CF.sub.3                                                                             H          H                                    EtO       CF.sub.3     Br     H          H                                    Et        SMe          CF.sub.3                                                                             H          H                                    Et        CF.sub.3     H      3-NHSO.sub.2 CF.sub.3                                                                    H                                    Et        CF.sub.3     H      3-NO.sub.2 H                                    FCH.sub.2 CH.sub.2 O                                                                    CF.sub.3     Cl     H          H                                    MeS       CF.sub.3     Br     H          H                                    EtS       CF.sub.3     CF.sub.3                                                                             H          H                                    n-butyl   CF.sub.3     Cl     H          H                                    CCH       CF.sub.3     Cl     H          H                                    HCCH.sub.2                                                                              CF.sub.3     CF.sub. 3                                                                            H          H                                    allyl     CF.sub.3     Cl     H          H                                    Me        CF.sub.3     Cl     H          F                                    Me        CF.sub.3     CF.sub.3                                                                             H          F                                    Et        CF.sub.3     H      3-CN       F                                    Et        CF.sub.3     H      3-SO.sub.2 CF.sub.3                                                                      H                                    n-propyl  CF.sub.3     H      3-SCF.sub.3                                                                              H                                    n-propyl  Cl           CF.sub.3                                                                             H          H                                    Me        CF.sub.3     H      2-F        H                                    Me        CF.sub.3     H      4-F        H                                    Me        CF.sub.3     H      3-SO.sub.2 CH.sub.2 CH.sub.3                                                             H                                    Me        CF.sub.3     Cl     3-Cl       H                                    Me        CF.sub.3     Cl     2-Cl       H                                    n-propyl  CF.sub.3     Cl     H          H                                    Et        SCHF.sub.2   CF.sub.3                                                                             H          H                                    n-propyl  SCHF.sub.2   CF.sub.3                                                                             H          H                                    MeNH      CF.sub.3     CF.sub.3                                                                             H          H                                    Me.sub.2 N                                                                              CF.sub.3     CF.sub.3                                                                             H          H                                    Me        OCH.sub.2 CF.sub.3                                                                         CF.sub.3                                                                             H          F                                    n-propyl  CF.sub.3     H      3-CN       H                                    Et        CF.sub.3     H      3-CN       H                                    Me        OCF.sub.2 H  CF.sub.3                                                                             H          H                                    Me        OCF.sub.2 H  Cl     H          H                                    Me        OCF.sub.3    CF.sub.3                                                                             H          H                                    Me        OCF.sub.3    Cl     H          H                                    ______________________________________                                    

                  TABLE VI                                                        ______________________________________                                         ##STR21##                                                                    R.sub.1 R.sub.2    R.sub.4 R.sub.5  R.sub.6                                                                           R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                              H        H   H                                     Me      CF.sub.3   Cl      H        H   H                                     Et      CF.sub.3   Cl      H        H   H                                     Et      CF.sub.3   CF.sub.3                                                                              H        H   H                                     H       CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      SMe        Cl      H        H   H                                     Me      Cl         CF.sub.3                                                                              H        H   H                                     Me      SEt        CF.sub.3                                                                              H        H   H                                     Me      CF.sub.3   H       3-SCF.sub.3                                                                            H   H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                              H        H   CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                              H        H   H                                     Me      CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      CF.sub.3   Cl      H        H   CN                                    Me      CF.sub.3   CF.sub.3                                                                              H        F   CN                                    Me      CF.sub.3   CF.sub.3                                                                              H        H   Br                                    Et      CF.sub.3   CF.sub.3                                                                              H        H   CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      CF.sub.3   CF.sub.3                                                                              H        H   F                                     Et      CF.sub.3   Cl      H        H   CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                              H        H   H                                     Me      CF.sub.3   H       3-CN     H   H                                     MeO     CF.sub.3   CF.sub.3                                                                              H        H   H                                     F.sub.2 CH                                                                            CF.sub.3   Cl      H        H   H                                     Et      SMe        OMe     H        H   H                                     Me      CF.sub.3   CF.sub.3                                                                              H        F   H                                     Me      Cl         OMe     H        H   H                                     Me      CF.sub.3   Cl      H        F   H                                     isopropyl                                                                             CF.sub.3   Cl      H        H   H                                     MeS     CF.sub.3   Cl      H        H   H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl      H        H   H                                     Me      CF.sub.3   H       3-SO.sub.2 CF.sub.3                                                                    H   H                                     Me      CF.sub.3   H       3-SO.sub.2 Me                                                                          H   H                                     Et      Br         Cl      H        H   H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                              H        H   Cl                                    Me      CF.sub.3   Cl      H        H   NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                              H        F   H                                     Me      Cl         CF.sub.3                                                                              H        H   CN                                    Et      Cl         CF.sub.3                                                                              H        H   CN                                    Et      Cl         CF.sub.3                                                                              H        H   N                                     Me      SCHF.sub.2 CF.sub.3                                                                              H        H   H                                     Et      CF.sub.3   H       3-CN     H   H                                     Me      SCHF.sub.2 CF.sub.3                                                                              H        H   CN                                    Et      CF.sub.3   H       3-OCHF.sub.2                                                                           H   H                                     Me      CF.sub.3   H       3-OCHF.sub.2                                                                           H   CN                                    n-propyl                                                                              CF.sub.3   H       3-OCF.sub.3                                                                            H   CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Et      Br         CF.sub.3                                                                              H        H   H                                     Et      CF.sub.3   OMe     H        H   CN                                    Me      CF.sub.3   CF.sub.3                                                                              H        H   Me                                    Et      CF.sub.3   Cl      H        H   CO.sub.2 Me                           Me      CF.sub.3   H       3-OCH.sub.2 CF.sub.3                                                                   H   CN                                    Me      CF.sub.3   H       3-SCF.sub.3                                                                            H   CN                                    Et      CF.sub.3   H       3-SCHF.sub.2                                                                           H   CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      Cl         CF.sub.3                                                                              H        H   Cl                                    Et      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                              H        H   CN                                    Me      Cl         CF.sub.3                                                                              H        H   CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                              H        H   CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                              H        H   CN                                    Me      CF.sub.3   H       3-CN     H   CN                                    n-propyl                                                                              CF.sub.3   H       3-CN     H   CN                                    Et      CF.sub.3   H       3-SMe    H   CN                                    Et      Cl         H       3-CN     H   H                                     Me      SCHF.sub.2 CF.sub.3                                                                              H        H   H                                     Me      CF.sub.3   Br      H        H   CN                                    HCC     CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      CF.sub.3   H       3-SO.sub.2 CHF.sub.2                                                                   H   CN                                    Me      CF.sub.3   Cl      3-Cl     H   CN                                    Me      CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                              H        H   CN                                    Et      CHF.sub.2  CF.sub.3                                                                              H        H   CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                              H        H   CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H       H        H   H                                     Me      CF.sub.3   CF.sub.3                                                                              H        H   CONH.sub.2                            Me      CF.sub.3   Cl      H        H   CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                              H        H   NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                              H        H   CO.sub.2 Et                           Me      CF.sub.3   Cl      H        H   CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                              H        H   CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                              H        H   H                                     Me      OCF.sub.2 H                                                                              Cl      H        H   CN                                    Me      OCF.sub.2 H                                                                              Cl      H        H   H                                     Me      OCF.sub.3  CF.sub.3                                                                              H        H   CN                                    Me      OCF.sub.3  CF.sub.3                                                                              H        H   H                                     ______________________________________                                    

                  TABLE VII                                                       ______________________________________                                         ##STR22##                                                                    R.sub.1 R.sub.2    R.sub.4                                                                              R.sub.5  R.sub.6                                                                            R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   CF.sub.3                                                                             H        H    H                                     H       CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SMe        Cl     H        H    H                                     Me      Cl         CF.sub.3                                                                             H        H    H                                     Me      SEt        CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   Cl     H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        F    CN                                    Me      CF.sub.3   CF.sub. 3                                                                            H        H    Br                                    Et      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    F                                     Et      CF.sub.3   Cl     H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-CN     H    H                                     MeO     CF.sub.3   CF.sub.3                                                                             H        H    H                                     F.sub.2 CH                                                                            CF.sub.3   Cl     H        H    H                                     Et      SMe        OMe    H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         OMe    H        H    H                                     Me      CF.sub.3   Cl     H        F    H                                     isopropyl                                                                             CF.sub.3   Cl     H        H    H                                     MeS     CF.sub.3   Cl     H        H    H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl     H        H    H                                     Me      CF.sub.3   H      3-SO.sub.2 CF.sub.3                                                                    H    H                                     Me      CF.sub.3   H      3-SO.sub.2 Me                                                                          H    H                                     Et      Br         Cl     H        H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    Cl                                    Me      CF.sub.3   Cl     H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    N                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Et      CF.sub.3   H      3-OCHF.sub.2                                                                           H    H                                     Me      CF.sub.3   H      3-OCHF.sub.2                                                                           H    CN                                    n-propyl                                                                              CF.sub.3   H      3-OCF.sub.3                                                                            H    CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Et      Br         CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   OMe    H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Me                                    Et      CF.sub.3   Cl     H        H    CO.sub.2 Me                           Me      CF.sub.3   H      3-OCH.sub.2 CF.sub.3                                                                   H    CN                                    Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    CN                                    Et      CF.sub.3   H      3-SCHF.sub.2                                                                           H    CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    Cl                                    Et      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-CN     H    CN                                    n-propyl                                                                              CF.sub.3   H      3-CN     H    CN                                    Et      CF.sub.3   H      3-SMe    H    CN                                    Et      Cl         H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Br     H        H    CN                                    HCC     CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-SO.sub.2 CHF.sub.2                                                                   H    CN                                    Me      CF.sub.3   Cl     3-Cl     H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                             H        H    CN                                    Et      CHF.sub.2  CF.sub.3                                                                             H        H    CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H      H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CONH.sub.2                            Me      CF.sub.3   Cl     H        H    CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                             H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        H    CO.sub.2 Et                           Me      CF.sub.3   Cl     H        H    CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    H                                     Me      OCF.sub.2 H                                                                              Cl     H        H    CN                                    Me      OCF.sub.2 H                                                                              Cl     H        H    H                                     Me      OCF.sub.3  CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.3  CF.sub.3                                                                             H        H    H                                     ______________________________________                                    

                  TABLE VIII                                                      ______________________________________                                         ##STR23##                                                                    R.sub.1 R.sub.2    R.sub.4                                                                              R.sub.5  R.sub.6                                                                            R.sub.7                               ______________________________________                                        Me      CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   Cl     H        H    H                                     Et      CF.sub.3   CF.sub.3                                                                             H        H    H                                     H       CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SMe        Cl     H        H    H                                     Me      Cl         CF.sub.3                                                                             H        H    H                                     Me      SEt        CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   Cl     H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        F    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Br                                    Et      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    F                                     n-propyl                                                                              CF.sub.3   CF.sub.3                                                                             H        H    H                                     Me      CF.sub.3   H      3-CN     H    H                                     MeO     CF.sub.3   CF.sub.3                                                                             H        H    H                                     F.sub.2 CH                                                                            CF.sub.3   Cl     H        H    H                                     Et      SMe        OMe    H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         OMe    H        H    H                                     Me      CF.sub.3   Cl     H        F    H                                     isopropyl                                                                             CF.sub.3   Cl     H        H    H                                     MeS     CF.sub.3   Cl     H        H    H                                     MeOCH.sub.2                                                                           CF.sub.3   Cl     H        H    H                                     Me      CF.sub.3   H      3-SO.sub.2 CF.sub.3                                                                    H    H                                     Me      CF.sub.3   H      3-SO.sub.2 Me                                                                          H    H                                     Et      Br         Cl     H        H    H                                     Me      OCH.sub.2 CF.sub.3                                                                       CF.sub.3                                                                             H        H    Cl                                    Me      CF.sub.3   Cl     H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        F    H                                     Me      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    CN                                    Et      Cl         CF.sub.3                                                                             H        H    N                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub.3                                                                             H        H    CN                                    Et      CF.sub.3   H      3-OCHF.sub.2                                                                           H    H                                     Me      CF.sub.3   H      3-OCHF.sub.2                                                                           H    CN                                    n-propyl                                                                              CF.sub.3   H      3-OCF.sub.3                                                                            H    CN                                    MeOCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Et      Br         CF.sub.3                                                                             H        H    H                                     Et      CF.sub.3   OMe    H        H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    Me                                    Et      CF.sub.3   Cl     H        H    CO.sub.2 Me                           Me      CF.sub.3   H      3-OCH.sub.2 CF.sub.3                                                                   H    CN                                    Me      CF.sub.3   H      3-SCF.sub.3                                                                            H    CN                                    Et      CF.sub.3   H      3-SCHF.sub.2                                                                           H    CN                                    MeSCH.sub.2                                                                           CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    Cl                                    Et      OCH.sub.2 CHF.sub.2                                                                      CF.sub.3                                                                             H        H    CN                                    Me      Cl         CF.sub.3                                                                             H        H    CF.sub.3                              MeNH    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me.sub.2 N                                                                            CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CHF.sub.2                                                                       CF.sub.3                                                                             H        H    CN                                    Me      SO.sub.2 CH.sub.3                                                                        CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-CN     H    CN                                    n-propyl                                                                              CF.sub.3   H      3-CN     H    CN                                    Et      CF.sub.3   H      3-SMe    H    CN                                    Et      Cl         H      3-CN     H    H                                     Me      SCHF.sub.2 CF.sub. 3                                                                            H        H    H                                     Me      CF.sub.3   Br     H        H    CN                                    HCC     CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.3   H      3-SO.sub.2 CHF.sub.2                                                                   H    CN                                    Me      CF.sub.3   Cl     3-Cl     H    CN                                    Me      CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      CF.sub.2 Cl                                                                              CF.sub.3                                                                             H        H    CN                                    Et      CHF.sub.2  CF.sub.3                                                                             H        H    CN                                    FCH.sub.2 CH.sub.2                                                                    CF.sub.3   CF.sub.3                                                                             H        H    CN                                    Me      OCH.sub.2 CF.sub.3                                                                       H      H        H    H                                     Me      CF.sub.3   CF.sub.3                                                                             H        H    CONH.sub.2                            Me      CF.sub.3   Cl     H        H    CONH.sub.2                            Me      CF.sub.3   CF.sub.3                                                                             H        H    NO.sub.2                              Me      CF.sub.3   CF.sub.3                                                                             H        H    CO.sub.2 Et                           Me      CF.sub.3   Cl     H        H    CO.sub.2 Et                           Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.2 H                                                                              CF.sub.3                                                                             H        H    H                                     Me      OCF.sub.2 H                                                                              Cl     H        H    CN                                    Me      OCF.sub.2 H                                                                              Cl     H        H    H                                     Me      OCF.sub.3  CF.sub.3                                                                             H        H    CN                                    Me      OCF.sub.3  CF.sub.3                                                                             H        H    H                                     ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

    ______________________________________                                                    Weight Percent*                                                               Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE A

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         80%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                  13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE B

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        7-(3-ch1orophenyl)-5-methyl-2-(trifluoromethyl)-                                                         50%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               sodium alkylnaphthalenesulfonate                                                                          2%                                                low viscosity methyl cellulose                                                                            2%                                                diatomaceous earth         46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE C

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of Example 11                                                                         5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE D

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         25%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               anhydrous sodium sulfate   10%                                                crude calcium ligninsulfonate                                                                             5%                                                sodium alkylnaphthalenesulfonate                                                                          1%                                                calcium/magnesium bentonite                                                                              59%                                                ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE E

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                          1%                                                1,2,4-triazolo[1,5-a]Pyrimidine                                               N,N-dimethylformamide       9%                                                attapulgite granules       90%                                                (U.S.S. 20 to 40 sieve)                                                       ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE F

    ______________________________________                                        Granule                                                                       ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         80%                                                1, 2,4-triazolo[1,5-a]pyrimidine                                              wetting agent               1%                                                crude ligninsulfonate salt (containing                                                                   10%                                                5-20 of the natural sugars)                                                   attapulgite clay            9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE G

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         40%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               polyacrylic acid thickener 0.3%                                               dodecylphenol polyethylene glycol ether                                                                  0.5%                                               disodium phosphate          1%                                                monosodium phosphate       0.5%                                               polyvinyl alcohol          1.0%                                               water                      56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE H

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         99%                                                1,2,4-triazolo[1,5-a]Pyrimidine                                               silica aerogel             0.5%                                               synthetic amorphous silica 0.5%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE I

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         90%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               dioctyl sodium sulfosuccinate                                                                            0.1%                                               synthetic fine silica      9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below microns. The material is sifted througha U.S.S. No. 50 screen and then packaged.

EXAMPLE J

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         40%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               sodium ligninsulfonate     20%                                                montmorillonite clay       40%                                                ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE K

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         35%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               blend of polyalcohol carboxylic esters and                                                                6%                                                oil soluble petroleum sulfonates                                              xylene                     59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE L

    ______________________________________                                        Dust                                                                          ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         10%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               attapulgite                10%                                                Pyrophyllite               80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE M

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        7-(3-chlorophenyl)-5-methyl-2-(trifluoromethyl)-                                                         25%                                                1,2,4-triazolo[1,5-a]pyrimidine                                               polyoxyethylene sorbitol hexaoleate                                                                       5%                                                highly aliphatic hydrocarbon oil                                                                         70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

Utility

Test results indicate that compounds of the present invention are highlyactive preemergent and/or postemergent herbicides or plant growthregulants. Many of the compounds have utility for pre- and/orpostemergence broad-spectrum grass and broadleaf weed control in areaswhere complete control of all vegetation is desired, such as aroundstorage tanks, industrial storage areas, parking lots, drive-intheaters, around billboards, highways, and railroad structures, and infallow crop areas. Some compounds have utility in crops such as barley(Hordeum spp.), corn (Zea spp.), cotton (Gossypium spp.), pea (Pisumspp.), peanut (Arachis spp.), rape (Brassica spp.), rice (Oryza spp.),sorghum (Sorghum spp.), soybean (Glycine spp.), sugar beet (Beta spp ),sunflower (Helianthus spp.), triticale (Triticum-Secale spp.), and wheat(Triticum spp.). Some compounds are particularly useful for preemergencecontrol of troublesome grass and selected small-seeded broadleaf weedsin barley, corn, cotton, rice, soybean, and wheat. In cereal crops suchas barley, triticale, and wheat, some compounds are particularly usefulfor preemergence control of grass weeds such as blackgrass (Alopecurusmyosuroides), foxtail (Setaria spp.), and wild oat (Avena fatua), andselected broadleaf weeds such as kochia (Kochia scoparia), lambsquarters(Chenopodium album), and wild buckwheat (Polygonum convolvulvus). Inrice, some compounds are particularly useful for the control ofbarnyardgrass (Echinochloa crus-galli). In cotton, some compounds areparticularly useful for the control of barnyardgrass (Echinochloacrus-galli), bermudagrass (Cynodon dactylon), panicum (Panicum spp.),goosegrass (Eleusine spp.), crabgrass (Digitaria spp.), and pigweed(Amaranthus spp.).

In addition, many compounds of this invention are useful for the controlof weeds in plantation crops such as banana, citrus crops, cocoa,coffee, palm, rubber, sugar cane, etc. Several of these compounds arealso useful for weed control in fruit crops such as cranberries, apples,pears, cherries, etc. Several compounds of this invention areparticularly useful for the control of troublesome grass weeds in sugarcane (Saccharum spp.). Alternatively, the subject compounds are usefulto modify plant growth.

The rates of application for compounds of this invention are determinedby a number of factors, including their use as plant growth modifiers oras herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.004 to 20kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required, such asa herbicide for fallow land. Preferred rates of application are from0.025 to 2.0 kg/ha. One skilled in the art can easily determine theapplication rate needed for the desired level of weed control.

The compounds of the invention may be used in combination with any othercommercial herbicide, representative examples of which are those of thesulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether,carbamate, imidazolinone, cineole and bipyridylium types. A partiallisting follows:

    ______________________________________                                        Common Name   Chemical Name                                                   ______________________________________                                        acetochlor    2-chloro-N-(ethoxymethyl)-N-(2-                                               ethyl-6-methylphenyl)acetamide                                  acifluorfen   5-[2-chloro-4-(trifluoromethyl)                                               phenoxy]-2-nitrobenzoic acid                                    acrolein      2-propenal                                                      alachlor      2-chloro-N-(2,6-diethylphenyl)-                                               N-(methoxy-methyl)acetamide                                     ametryn       N-ethyl-N'-(1-methylethyl)-6-                                                 (methylthio)-1,3,5-triazine-2,                                                4-diamine                                                       amitrole      1H-1,2,4-triazol-3-amine                                        AMS           ammonium sulfamate                                              asulam        methyl [(4-aminophenyl)sulfonyl]                                              carbamate                                                       atrazine      6-chloro-N-ethyl-N'-(1-methyl                                                 ethyl)-1,3,5-triazine-2,4-diamine                               barban        4-chloro-2-butynyl 3-chloro                                                   carbamate                                                       benefin       N-butyl-N-ethyl-2,6-dinitro-4-                                                (tri-fluoromethyl)benzenamine                                   bensulfuron   2-[[[[[(4,6-dimethoxy-2-pyrimi                                  methyl        dinyl)amino]-methylcarbonyl]amino]                                            sulfonyl]methyl]benzoic acid,                                                 methyl ester                                                    bensulide     O,O-bis(1-methylethyl) S-[2-                                                  [(phenylsulfonyl)amino]ethyl]                                                 phosphorodithioate                                              bentazon      3-(1-methylethyl)-(1H)-2,1,3-                                                 benzothia-diazin-4(3H)-one,                                                   2,2-dioxide                                                     benzofluor    N-[4-(ethylthio)-2-(trifluoro                                                 methyl)-phenyl]methanesulfonamide                               benzoylprop   N-benzoyl-N-(3,4-dichlorophenyl)-                                             DL-alanine                                                      bifenox       methyl 5-(2,4-dichlorophenoxy)-2-                                             nitrobenzoate                                                   bromacil      5-bromo-6-methyl-3-(1-methyl                                                  propyl)-2,4(1H,3H)pyrimidinedione                               bromoxynil    3,5-dibromo-4-hydroxybenzonitrile                               butachlor     N-(butoxymethyl)-2-chloro-N-(2,6-                                             diethyl-phenyl)acetamide                                        buthidazole   3-[5-(1,1-dimethylethyl)-1,3,4-thia-                                          diazol-2-yl]-4-hydroxy-1-methyl-2-                                            imidazolidinone                                                 butralin      4-(1,1-dimethylethyl)-N-(1-methyl-                                            propyl)-2,6-dinitrobenzenamine                                  butylate      S-ethyl bis(2-methylpropyl)-                                                  carbamothioate                                                  cacodylic     dimethyl arsinic oxide                                          acid                                                                          CDAA          2-chloro-N,N-di-2-propenylacetamide                             CDEC          2-chloroallyl diethyldithiocarbamate                            chloramben    3-amino-2,5-dichlorobenzoic acid                                chlorbromuron 3-(4-bromo-3-chlorophenyl)-1-methoxy-                                         1-methylurea                                                    chlorimuron   2-[[[[(4-chloro-6-methoxy-2-                                    ethyl         pyrimidinyl)amino]carbonyl]amino]-                                            sulfonyl]benzoic acid, ethyl ester                              chloroxuron   N'-[4-(4-Chlorophenoxy)phenyl]-N,N-                                           dimethylurea                                                    chlorpropham  1-methylethyl 3-chlorophenylcarbamate                           chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-                                       triazin-2-yl)amino]carbonyl]benzene-                                          sulfonamide                                                     chlortoluron  N'-(3-chloro-4-methylphenyl)-N,N-                                             dimethylurea                                                    cinmethylin   exo-1-methyl-4-(1-methylethyl)-2-[(2-                                         methylphenyl)methoxy]-7-oxabicyclo-                                           [2.2.1]heptane                                                  clethodim     (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)-                                    oxy]imino]propyl]-5-[2-(ethylthio)-                                           propyl]-3-hydroxy-2-cyclohexen-1-one                            clomazone     2-[(2-chlorophenyl)methyl]-4,4-                                               dimethyl-3-isoxazolidinone                                      cloproxydim   (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)-                                       imino]butyl]-5-[2-(ethylthio)propyl]-                                         3-hydroxy-2-cyclohexen-1-one                                    clopyralid    3,6-dichloro-2-pyridinecarboxylic acid                          CMA           calcium salt of MAA                                             cyanazine     2-[[4-chloro-6-(ethylamino)-1,3,5-tri-                                        azin-2-yl]amino]-2-methylpropanenitrile                         cycloate      S-ethyl cyclohexylethylcarbamothioate                           cycluron      3-cyclooctyl-1,1-dimethylurea                                   cyperquat     1-methyl-4-phenylpyridinium                                     cyprazine     2-chloro-4-(cyclopropylamino)-6-(iso-                                         propylamino)- .sub.- s-triazine                                 cyprazole     N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-                                      thiadiazol-2-yl]cyclopropanecarbox-                                           amide                                                           cypromid      3',4'-dichlorocyclopropanecarboxanilide                         dalapon       2,2-dichloropropanoic acid                                      dazomet       tetrahydro-3,5-dimethyl-2H-1,3,5-thia-                                        diazine-2-thione                                                DCPA          dimethyl 2,3,5,6-tetrachloro-1,4-                                             benzene-dicarboxylate                                           desmediphan   ethyl [3-[[(phenylamino)carbonyl]oxy]-                                        phenyl]carbamate                                                desmetryn     2-(isopropylamino)-4-(methylamino)-6-                                         (methylthio)- .sub.- s-triazine                                 diallate      S-(2,3-dichloro-2-propenyl)bis(1-                                             methylethyl)carbamothioate                                      dicamba       3,6-dichloro-2-methoxybenzoic acid                              dichlobenil   2,6-dichlorobenzonitrile                                        dichlorprop   (±)-2-(2,4-dichlorophenoxy)-                                               propanoic acid                                                  dichlofop     (±)-2-[4-(2,4-dichlorophenoxy)-                                            phenoxy]propanoic acid                                          diethatyl     N-(chloroacetyl)-N-(2,6-diethylphenyl)-                                       glycine                                                         difenzoquat   1,2-dimethyl-3,5-diphenyl-1H-                                                 pyrazolium                                                      dinitramine   N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(trifluoro-                            methyl)-1,3-benzenediamine                                      dinoseb       2-(1-methylpropyl)-4,6-dinitrophenol                            diphenamid    N,N-dimethyl-α-phenylbenzene-                                           acetamide                                                       dipropetryn   6-(ethylthio)-N,N'-bis(1-methylethyl)-                                        1,3,5-triazine-2,4-diamine                                      diquat        6,7-dihydrodipyrido[1,2-a:2',1'-c]-                                           pyrazinedium ion                                                diuron        N'-(3,4-dichlorophenyl)-N,N-                                                  dimethylurea                                                    DNOC          2-methyl-4,6-dinitrophenol                                      DPX-M6316     3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-                                      2-yl)amino]carbonyl]amino]sulfonyl]-                                          2-thiophenecarboxylic acid, methyl                                            ester                                                           DSMA          disodium salt of MAA                                            endothall     7-oxabicyclo[2.2.1]heptane-2,3-dicarbox-                                      ylic acid                                                       EPTC          S-ethyl dipropylcarbamothioate                                  ethalfluralin N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                          dinitro-4-(trifluoromethyl)-                                                  benzenamin                                                      ethofumesate  (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-                                     5-benzofuranyl methanesulfonate                                 Express ® 2-[[[[N-(4-methoxy-6-methyl-1,3,5-                                            triazine-2-yl)-N-methylamino]carbonyl]-                                       amino]sulfonyl]benzoic acid,                                                  methyl ester                                                    fenac         2,3,6-trichlorobenzeneacetic acid                               fenoxaprop    (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]-                                   phenoxy]propanoic acid                                          fenuron       N,N-dimethyl-N'-phenylurea                                      fenuron TCA   Salt of fenuron and TCA                                         flamprop      N-benzoyl-N-(3-chloro-4-fluorophenyl)-                                        DL-alanine                                                      fluazifop     (±)-2-[4-[[5-(trifluoromethyl)-2-pyri-                                     dinyl]oxy]phenoxy]propanoic acid                                fluazifop-P   (R)-2-[4-[[5-(trifluoromethyl)-2-pyri-                                        dinyl]oxy]phenoxy]propanoic acid                                fluchloralin  N-(2-chloroethyl)-2,6-dinitro-N-propyl-                                       4-(trifluoromethyl)benzenamine                                  fluometuron   N,N-dimethyl-N'-[3-(trifluoromethyl)-                                         phenyl]urea                                                     fluorochlor-  3-chloro-4-(chloromethyl)-1-[3-(tri-                            idone         fluoromethyl)phenyl]-2-pyrrolidinone                            fluorodifen    -p-nitrophenyl α, α,α-trifluoro-2-nitro-                   2                                                                              -p-tolyl ether                                                 fluoroglycofen                                                                              carboxymethyl 5-[2-chloro-4-(tri-                                             fluoromethyl)phenoxy]-2-nitrobenzoate                           fluridone     1-methyl-3-phenyl-5-[3-(trifluoro-                                            methyl)phenyl]-4(1H)-pyridinone                                 fomesafen     5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                      N-(methylsulfonyl)-2-nitrobenzamide                             fosamine      ethyl hydrogen (aminocarbonyl)-                                               phosphate                                                       glyphosate    N-(phosphonomethyl)glycine                                      haloxyfop     2-[4-[[3-chloro-5-(trifluoromethyl)-2-                                        pyridinyl]oxy]phenoxy]propanoic acid                            hexaflurate   potassium hexafluoroarsenate                                    hexazinone    3-cyclohexyl-6-(dimethylamino)-1-                                             methyl-1,3,5-triazine-2,4(1H,3H)-dione                          imazamethabenz                                                                              6-(4-isopropyl-4-methyl-5-oxo-2-                                              imidazolin-2-yl)- .sub.-- m-toluic acid,                                      methyl ester and 6-(4-isopropyl-                                              4-methyl-5-oxo-2-imidazolin-2-yl)-                                             -p-toluic acid, methyl ester                                   imazapyr      (±)-2-[4,5-dihydro-4-methyl-4-(1-                                          methylethyl)-5-oxo-1H-imidazol-2-yl]-3-                                       pyridinecarboxylic acid                                         imazaquin     2-[4,5-dihydro-4-methyl-4-(1-methyl-                                          ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                             quinolinecarboxylic acid                                        imazethapyr   (±)-2-[4,5-dihydro 4-methyl-4-(1-                                          methylethyl)-5-oxo-1H-imidazol-2-yl]-5-                                       ethyl-3-pyridinecarboxylic acid                                 ioxynil       4-hydroxy-3,5-diiodobenzonitrile                                isopropalin   4-(1-methylethyl)-2,6-dinitro-N,N-                                            dipropylbenzenamine                                             isoproturon   N-(4-isopropylphenyl)-N',N'-                                                  dimethylurea                                                    isouron       N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]-                                      N,N-dimethylurea                                                isoxaben      N-[3-(1-ethyl-1-methylpropyl)-5-                                              isoxazolyl]-2,6-dimethoxybenzamide                              karbutilate   3-[[(dimethylamino)carbonyl]amino] 9 -                                        phenyl-(1,1-dimethylethyl)carbamate                             lactofen      (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-                                     chloro-4-(trifluoromethyl)phenoxy]-                                           2-nitrobenzoate                                                 lenacil       3-cyclohexyl-6,7-dihydro-1H-cyclopenta-                                       Pyrimidine-2,4(3H,5H)-dione                                     linuron       N'-(3,4-dichlorophenyl)-N-methoxy-N-                                          methylurea                                                      MAA           methylarsonic acid                                              MAMA          monoammonium salt of MAA                                        MCPA          (4-chloro-2-methylphenoxy)acetic acid                           MCPB          4-(4-chloro-2-methylphenoxy)butanoic                                          acid                                                            mecoprop      (±)-2-(4-chloro-2-methylphenoxy)-                                          propanoic acid                                                  mefluidide    N-[2,4-dimethyl-5-[[(trifluoromethyl)-                                        sulfonyl]amino]phenyl]acetamide                                 methal-       N-(2-methyl-2-propenyl)-2,6-dinitro-N-                          propalin      propyl-4-(trifluoromethyl)benzenamide                           methabenz-    1,3-dimethyl-3-(2-benzothiazolyl)urea                           thiazuron                                                                     metham        methylcarbamodithioic acid                                      methazole     2-(3,4-dichlorophenyl)-4-methyl-1,2,4-                                        oxadiazolidine-3,5-dione                                        methoxuron    N'-(3-chloro-4-methoxyphenyl)-N,N-                                            dimethylurea                                                    metolachlor   2-chloro-N-(2-ethyl-6-methylphenyl)-N-                                        (2-methoxy-1-methylethyl)acetamide                              metribuzin    4-amino-6-(1,1-dimethylethyl)-3-(methyl-                                      thio)-1,2,4-triazin-5(4H)-one                                   metsulfuron   2-[[[[(4-methoxy-6-methyl-1,3,5-tri-                            methyl        azin-2-yl)amino]carbonyl]-                                                    amino]sulfonyl]benzoic acid,                                                  methyl ester                                                    MH            1,2-dihydro-3,6-pyridazinedione                                 molinate      S-ethyl hexahydro-1H-azepine-1-carbo-                                         thioate                                                         monolinuron   3-( -p-chlorophenyl)-1-methoxy-1-methyl-                                      urea                                                            monuron       N'-(4-chlorophenyl)-N,N-dimethylurea                            monuron TCA   Salt of monuron and TCA                                         MSMA          monosodium salt of MAA                                          napropamide   N,N-diethyl-2-(1-naphthalenyloxy)-                                            propanamide                                                     naptalam      2-[(1-naphthalenylamino)carbonyl]-                                            benzoic acid                                                    neburon       1-butyl-3-(3,4-dichlorophenyl)-1-methyl-                                      urea                                                            nitralin      4-(methylsulfonyl)-2,6-dinitro-N,N-                                           dipropylaniline                                                 nitrofen      2,4-dichloro-1-(4-nitrophenoxy)benzene                          nitrofluorfen 2-chloro-1-(4-nitrophenoxy)-4-(tri-                                           fluoromethyl)benzene                                            norea         N,N-dimethyl-N'-(octahydro-4,7-                                               methano-1H-inden-5-yl)urea 3aα,-                                        4α,5α,7α,7aα-isomer                     norflurazon   4-chloro-5-(methylamino)-2-[3-(tri-                                           fluromethyl)phenyl]-3(2H)-pyridazinon                           oryzalin      4-(dipropylamino)-3,5-dinitro-                                                benzenesulfonamide                                              oxadiazon     3-[2,4-dichloro-5-(1-methylethoxy)-                                           phenyl]-5-(1,1-dimethylethyl)-                                                1,3,4-oxadiazol-2(3H)-one                                       oxyfluorfen   2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-                                       (trifluoromethyl)benzene                                        paraquat      1,1'-dimethyl-4,4'-dipyridinium ion                             pebulate      S-propyl butylethylcarbamothioate                               pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                           dinitrobenzenamine                                              perfluidone   1,1,1-trifluoro-N-[2-methyl-4-(phenyl-                                        sulfonyl)phenyl]methanesulfonamide                              phenmedipham  3-[(methoxycarbonyl)amino]phenyl (3-                                          methylphenyl)carbamate                                          picloram      4-amino-3,5,6-trichloro-2-pyridine-                                           carboxylic acid                                                 PPG-1013      5-[2-chloro-4-(trifluoromethyl)-                                              phenoxy]-2-nitroacetophenone                                                  oxime-O-acetic acid, methyl ester                               procyazine    2-[[4-chloro-6-(cyclopropylamino)-1,3,5-                                      triazine-2-yl]amino]-2-methylpropane-                                         nitrile                                                         profluralin   N-(cyclopropylmethyl)-2,6-dinitro-N-                                          propyl-4-(trifluoromethyl)benzenamine                           prometon      6-methoxy-N,N'-bis(1-methylethyl)-                                            1,3,5-triazine-2,4-diamine                                      Prometryn     N,N'-bis(1-methylethyl)-6-(methylthio)-                                       1,3,5-triazine-2,4-diamine                                      pronamide     3,5-dichloro-N-(1,1-dimethyl-2-propyn-                                        yl)benzamide                                                    propachlor    2-chloro-N-(1-methylethyl)-N-                                                 phenylacetamide                                                 propanil      N-(3,4-dichlorophenyl)propanamide                               propazine     6-chloro-N,N'-bis(1-methylethyl)-                                             1,3,5-triazine-2,4-diamine                                      propham       1-methylethyl phenylcarbamate                                   prosulfalin   N-[[4-(dipropylamino)-3,5-dinitro-                                            phenyl]sulfonyl]-S,S-dimethylsulfil-                                          imine                                                           prynachlor    2-chloro-N-(1-methyl-2-propynyl)acet-                                         anilide                                                         pyrazon       5-amino-4-chloro-2-phenyl-3(2H)-                                              pyridazinone                                                    quizalofop    (±)-2-[4-[(6-chloro-2-quinoxalinyl)-                         ethyl         oxy]phenoxy]propanoic acid, ethyl                                             ester                                                           secbumeton    N-ethyl-6-methoxy-N'-(1-methylpropyl)-                                        1,3,5-triazine-2,4-diamine                                      sethoxydim    2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                         thio)propyl]-3-hydroxy-2-cyclohexen-                                          1-one                                                           siduron       N-(2-methylcyclohexyl)-N'-phenylurea                            simazine      6-chloro-N,N'-diethyl-1,3,5-triazine-                                         2,4-diamine                                                     sulfometuron  2-[[[[(4,6-dimethyl-2-pyrimidinyl)-                             methyl        amino]carbonyl]amino]sulfonyl]-                                               benzoic acid, methyl ester                                      TCA           trichloroacetic acid                                            tebuthiuron   N-[5-(1,1-dimethylethyl)-1,3,4-thiadi-                                        azol-2-yl]-N,N'-dimethylurea                                    terbacil      5-chloro-3-(1,1-dimethylethyl)-6-                                             methyl-2,4(1H,3H)-pyrimidinedione                               terbuchlor    N-(butoxymethyl)-2-chloro-N-[2-(1,1-                                          dimethylethyl)-6-methylphenyl]-                                               acetamide                                                       terbuthyl-    2-(tert-butylamino)-4-chloro-6-(ethyl-                          azine         amino)- .sub.- s-triazine                                       terbutol      2,6-di-tert-butyl- -p-tolyl methylcar-                                        bamate                                                          terbutryn     N-(1,1-dimethylethyl)-N'-ethyl-6-                                             (methylthio)-1,3,5-triazine-                                                  2,4-diamine                                                     thiobencarb   S-[(4-chlorophenyl)methyl] diethylcar-                                        bamothioate                                                     triallate     S-(2,3,3-trichloro-2-propenyl) bis(1-                                         methylethyl)carbamothioate                                      triclopyr     [(3,5,6-trichloro-2-pyridinyl)-                                               oxy]acetic acid                                                 tridiphane    2-(3,5-dichlorophenyl)-2-(2,2,2-                                              trichloroethyl)oxirane                                          trifluralin   2,6-dinitro-N,N-dipropyl-4-(tri-                                              fluoromethyl)benzenamine                                        trimeturon    1-( -p-chlorophenyl)-2,3,3-trimethylpseu-                                     dourea                                                          2,4-D         (2,4-dichlorophenoxy)acetic acid                                2,4-DB        4-(2,4-dichlorophenoxy)butanoic acid                            vernolate     S-propyl dipropylcarbamothioate                                 xylachlor     2-chloro-N-(2,3-dimethylphenyl)-N-                                            (1-methylethyl)acetamide                                        ______________________________________                                    

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

                                      TABLE OF COMPOUNDS                          __________________________________________________________________________    CMPD                                                                              R.sub.1                                                                              R.sub.2 R.sub.4                                                                             R.sub.5                                                                              R.sub.6                                                                         m.p. °C.                             __________________________________________________________________________     ##STR24##                                                                    1   Me     SMe     H     H      H 76-79                                       2   Me     SO.sub.2 Me                                                                           H     H      H 158-159                                     3   Me     CF.sub.3                                                                              H     H      H 106-108                                     4   Me     CF.sub.3                                                                              H     4-Cl   H 147-148                                     5   Me     CF.sub.3                                                                              OMe   H      H 102-104                                     6   BrCH.sub.2                                                                           CF.sub.3                                                                              OMe   H      H 94-98                                       7   Br.sub.2 CH                                                                          CF.sub.3                                                                              OMe   H      H 123-128                                     8   Me     CHF.sub.2                                                                             CF.sub.3                                                                            H      H 113-115                                     9   Me     CF.sub.3                                                                              H     2-Cl   H 149-150                                     10  CF.sub.3                                                                             CF.sub.3                                                                              H     H      H 120-121                                     11  Et     CF.sub.3                                                                              H     H      H  99-101                                     12  H      CF.sub.3                                                                              H     H      H 138-142                                     13  Me     CF.sub.3                                                                              F     H      H 113                                         14  Me     SOMe    H     H      H 136-137                                     15  Me     CF.sub.3                                                                              Cl    H      H 115-116                                     16  Me     SCF.sub.3                                                                             H     H      H 91-93                                       17  Me     CF.sub.2 Cl                                                                           CF.sub.3                                                                            H      H 115-117                                     18  Me     CF.sub.3                                                                              H     4-OMe  H 102-104                                     19  Me     Cl      H     H      H 179-181                                     20  Me     CF.sub.3                                                                              Me    H      H 110-111                                     21  Me     Br      H     H      H 178-180                                     22  Me     OMe     H     H      H 136-137                                     23  Me     CF.sub.3                                                                              CF.sub.3                                                                            H      H 133-134                                     24  Me     CF.sub.3                                                                              H     2-Me   H 109-110                                     25  Me     CF.sub.3                                                                              Br    H      H 110-112                                     26  Me     CF.sub.3                                                                              OMe   5-OMe  H 137-139                                     27  Me     CF.sub.3                                                                              OMe   2-OMe  H 152-153                                     28  Me     OCH.sub.2 CF.sub.3                                                                    H     H      H 103-104                                     29  Me     CF.sub.3                                                                              Me    4-Me   H 149-150                                     30  Me     SMe     Cl    H      H 140-142                                     31  Me     SO.sub.2 Me                                                                           Cl    H      H 162-163                                     32  Me     OCH.sub.2 CF.sub.3                                                                    Cl    H      H 156-157                                     33  Me     SCF.sub. 3                                                                            Cl    H      H 90-93                                       34  Me     Br      CF.sub.3                                                                            H      H 129-130                                     35  Me     C.sub.2 F.sub.5                                                                       CF.sub.3                                                                            H      H 103-104                                     36  Me     OCH.sub.2 CF.sub.3                                                                    CF.sub.3                                                                            H      H 157-159                                     37  Me     C.sub.2 F.sub.5                                                                       Cl    H      H 107-108                                     38  Me     SCH.sub.2 CF.sub.3                                                                    Cl    H      H 98-99                                       39  Me     SO.sub.2 CH.sub.2 CF.sub.3                                                            Cl    H      H 141-142                                     40  Me     OCH.sub.2 C.sub.2 F.sub.5                                                             CF.sub.3                                                                            H      H 159-160                                     41  OMe    CF.sub.3                                                                              H     H      H 157-158                                     42  Me     OCH.sub.2 CCl.sub.3                                                                   Cl    H      H 155-157                                     43  Me     SCHF.sub.2                                                                            Cl    H      H 145-146                                     44  Me     Cl      CF.sub.3                                                                            H      H 140-141                                     45  Me     Br      Cl    H      H 166-167                                     46  Me     SCHF.sub.2                                                                            CF.sub.3                                                                            H      H 140-141                                     47  Me     SO.sub.2 CHF.sub.2                                                                    CF.sub.3                                                                            H      H 96-98                                       48  Me     SCF.sub.3                                                                             CF.sub.3                                                                            H      H 144-145                                     49  Me     OSO.sub.2 CF.sub.3                                                                    Cl    H      H 131-133                                     50  Et     CF.sub.3                                                                              Cl    H      H 96-98                                       51  Me     CF.sub.3                                                                              H     3-NO.sub.2                                                                           H 206-208                                     52  n-butyl                                                                              CF.sub.3                                                                              Cl    H      H 66-69                                       53  Et     CF.sub.3                                                                              CF.sub.3                                                                            H      H 91-94                                       54  n-butyl                                                                              CF.sub.3                                                                              CF.sub.3                                                                            H      H 54-56                                       55  Et     CF.sub.3                                                                              Br    H      H 95-99                                       56  Me     CF.sub.3                                                                              H     3-CN   H 185-189                                     57  n-propyl                                                                             CF.sub.3                                                                              CF.sub.3                                                                            H      H 66-69                                       58  Me     CF.sub.3                                                                              H     H      F  99.5-100.5                                 59  iso-propyl                                                                           CF.sub.3                                                                              CF.sub.3                                                                            H      H 72-74                                       60  SMe    CF.sub.3                                                                              CF.sub.3                                                                            H      H 120-124                                     61  Me     CF.sub.3                                                                              H     3-OCF.sub.3                                                                          H 115-117                                     62  NMe.sub.2                                                                            CF.sub.3                                                                              CF.sub.3                                                                            H      H 183-185                                     63  OEt    CF.sub.3                                                                              CF.sub.3                                                                            H      H 158-160                                     64  OMe    CF.sub.3                                                                              CF.sub.3                                                                            H      H 142-145                                     65  SMe    CF.sub.3                                                                              Br    H      H 116-118                                     66  Me     SMe     CF.sub.3                                                                            H      H 173-175                                     67  Me     CF.sub.3                                                                              H     3-(CF.sub.2).sub.3 CF.sub.3                                                          H 93-95                                       68  Me     OCH.sub.2 CHF.sub.2                                                                   CF.sub.3                                                                            H      H 136-137                                     69  Me     OCH(Me)CF.sub.3                                                                       CF.sub.3                                                                            H      H 177-178                                     70  Et     CF.sub.3                                                                              Cl    3-Cl   H 185-190                                     71  n-propyl                                                                             CF.sub.3                                                                              Cl    H      H 86-88                                       72  Me     CF.sub.3                                                                              H     3-OPh  H 167-170                                     73  n-propyl                                                                             CF.sub.3                                                                              H     3-CN   H 109-110                                     74  Et     CF.sub.3                                                                              H     3-CN   H 164-167                                     83  Et     CF.sub.3                                                                              H     3-NMe.sub.2                                                                          H 88-90                                       84  Et     CF.sub.3                                                                              H     3-OCHF.sub.2                                                                         H 103-105                                     85  Me     CF.sub.3                                                                              H     3-SMe  H  95-100                                     86  Me     CF.sub.3                                                                              H     3-Ph   H 165-173                                     87  Me     CF.sub.3                                                                              H     3-OCHF.sub.2                                                                         H 96-99                                       88  Me     CF.sub.3                                                                              H     2-F    H 112-115                                     89  MeNH   CF.sub.3                                                                              CF.sub.3                                                                            H      H 191-194                                     90  MeNH   CF.sub.3                                                                              Br    H      H 215-218                                     91  Me     CF.sub.3                                                                              F     2-F    H 103-106                                     92  n-butyl                                                                              CF.sub.3                                                                              H     H      H 77-79                                       96  CF.sub.3                                                                             CF.sub.3                                                                              SCH.sub.2 Cl                                                                        H      H 96-99                                       97  CH.sub.3                                                                             SCH.sub.3                                                                             CN    H      H 202-204                                     98  CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                              SCHF.sub.2                                                                          H      H oil                                         99  CH.sub.3                                                                             CF.sub.3                                                                              I     H      H 93-95                                       100 CH.sub.2 CH3                                                                         CF.sub.3                                                                              SCF.sub.3                                                                           H      H 63-68                                       101 CH.sub.2 CH.sub.2 CH.sub.3                                                           Br      CF.sub.3                                                                            H      H 90-92                                       102 CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                              SO.sub.2 CHF.sub.2                                                                  H      H 136-140                                     103 CH.sub.2 CH.sub.2 CH.sub.3                                                           OCH.sub.2 CF.sub.3                                                                    CF.sub.3                                                                            H      H 77-80                                       104 CH.sub.3                                                                             CF.sub.3                                                                              CF.sub.2 CF.sub.3                                                                   H      H 146-149                                     105 CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                              SCF.sub.2 CF.sub.3                                                                  H      H oil                                         106 CH.sub.2 CH.sub.3                                                                    CF.sub.3                                                                              SO.sub.2 CF.sub.2 CF.sub.3                                                          H      H wax                                         109 CH.sub.2 CH.sub.3                                                                    Br      Br    H      H 132-135                                     110 CH.sub.2 CH.sub.3                                                                    OCH.sub.2 CF.sub.3                                                                    Br    H      H 93-95                                       111 CH.sub.3                                                                             CF.sub.3                                                                              Cl    2-OCH.sub.3                                                                          H 102-105                                     112 CH.sub.3                                                                             CF.sub.3                                                                              CF.sub.3                                                                            6-F    H 85-89                                       113 CH.sub.3                                                                             Br      OCF.sub.3                                                                           H      H 126-129                                     114 CH.sub.2 CH.sub.3                                                                    Br      Cl    H      H 130-133                                     115 CH.sub.3                                                                             OCH.sub.2 CF.sub.3                                                                    OCF.sub.3                                                                           H      H 141-143                                     116 CH.sub.2 CH.sub.3                                                                    OCH.sub.2 CF.sub.3                                                                    Cl    H      H oil                                         117 CH.sub.3                                                                             OCH.sub.3                                                                             CF.sub.3                                                                            H      H 173-174                                     118 CH.sub.3                                                                             OCHF.sub.2                                                                            CF.sub.3                                                                            H      H 102                                         __________________________________________________________________________    CMPD X   Y       Z   R.sub.2                                                                              R.sub.4                                                                           m.p. °C.                               __________________________________________________________________________     ##STR25##                                                                    75   N   CCN     N   CF.sub.3                                                                             H   110-115                                       76   N   CCN     N   CF.sub.3                                                                             CF.sub.3                                                                            125-126.5                                   94   N   CH      N   OCH.sub.2 CF.sub.3                                                                   H   101-103                                       95   N   CCN     N   CF.sub.3                                                                             Cl  178-179                                       120  CH  N       N   CF.sub.3                                                                             CF.sub.3                                                                          83-84                                          ##STR26##                                                                    77   N   CH      N   CF.sub.3                                                                             H     114-117.5                                   78   N   CBr     N   CF.sub.3                                                                             H   132-135                                       79   N   CH      N   CF.sub.3                                                                             CF.sub.3                                                                          122-123                                       80   N   N       N   CF.sub.3                                                                             H   108-110                                       81   N   CF      N   CF.sub.3                                                                             H     120-123.5                                   82   N   N       N   CF.sub.3                                                                             CF.sub.3                                                                            134-135.5                                   107  N   N       N   CF.sub.3                                                                             Cl  123-126                                       108  N   CCO.sub.2 Et                                                                          N   CF.sub.3                                                                             Cl  92-94                                         119  N   CCONH.sub.2                                                                           N   CF.sub.3                                                                             Cl  225-228                                       __________________________________________________________________________

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), cheatgrass, (Bromus secalinus), cocklebur (Xanthiumpensylvanicum), corn (Zea mays), cotton, (Gossypium hirsutum), crabgrass(Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoeaspp.), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycinemax), sugar beet (Beta volgaris), velvetleaf (pi Abutilon theophrasti),wheat (Triticum aestivum), and wild oat (Avena fatua) and purplenutsedge (Cyperus rotundus) tubers were planted and treated preemergencewith test chemicals dissolved in a non-phytotoxic solvent. At the sametime, these crop and weed species were also treated with postemergenceapplications of test chemicals. Plants ranged in height from two toeighteen cm (two to three leaf stage) for postemergence treatments.Treated plants and controls were maintained in a greenhouse forapproximately sixteen days, after which all species were compared tocontrols and visually evaluated. The ratings, summarized in Table A, arebased on a scale of 0 to 10 where 0 is no effect and 10 is completecontrol. A dash (-) response means no test result.

    TABLE A      POSTEMERGENCE COMPOUND (2000 g/ha) 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15     16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 3637       Barley -- -- 4 0 3 0 0 9 0 0 2 0 1 0 8 1 7 0 0 20 0 8 0 3 0 0 0 0 0 0     5 -- 4 4 0 7 Barnyardgrass 0 0 6 0 9 0 0 -- 0 0 9 2 8 1 9 5 -- 0 0 70 0     9 2 9 0 0 9 0 2 0 9 -- 9 9 4 9 Cheatgrass 0 0 0 0 7 0 0 8 0 0 2 0 2 0 8     2 8 0 0 2 0 0 8 0 8 0 0 2 0 0 2 9 -- 3 5 0 4 Cocklebur 2 3 5 1 8 3 2 8 2     0 6 1 7 3 6 4 8 0 1 6 1 2 9 1 6 1 1 5 0 2 2 9 -- 6 8 5 9 Corn 0 0 4 0 6     0 0 9 0 0 7 0 7 0 8 6 7 0 0 6 0 0 9 0 7 0 0 8 0 0 5 8 -- 5 5 2 7 Cotton     2 6 7 2 9 9 7 10  4 0 7 1 10  7 10  9 10  0 1 9 0 0 9 5 10  1 1 5 0 1 7     10  -- 10  10  9 -- Crabgrass 0 6 7 3 7 2 2 9 0 0 10  0 8 2 9 8 -- 0 0 8     1 0 9 8 9 8 1 9 0 5 7 9 -- 10  10  5 9 Giant Foxtail -- -- 7 0 9 0 0 9 0     0 8 0 8 2 9 6 9 0 0 5 2 0 9 9 9 7 2 9 1 6 8 9 -- 9 9 3 10  Morningglory     5 5 7 5 8 3 6 9 5 0 7 2 9 3 9 8 9 1 2 3 6 1 9 9 9 1 3 8 1 5 7 9 -- 8 9 7     10  Nutsedge 0 0 4 0 7 0 0 9 0 0 2 0 5 0 6 3 7 0 0 -- 0 0 9 -- 8 0 0 5 0     0 4 5 -- 8 3 0 5 Rice 0 0 3 1 8 1 0 9 0 0 5 2 8 0 8 3 8 0 0 5 1 0 9 0 8     3 2 2 0 0 0 5 -- 3 4 0 6 Sorghum 0 0 2 0 7 1 0 9 0 0 2 0 5 0 7 0 7 0 0 2     0 0 8 0 8 0 0 5 0 3 2 7 -- 6 7 1 7 Soybean 3 8 7 3 8 8 2 9 7 3 9 2 9 4 9     9 9 0 6 9 6 6 9 6 9 4 2 9 3 5 8 9 -- 10  10  7 9 Sugar beet 5 2 7 3 9 8     3 9 5 0 8 2 9 3 10  8 9 0 7 9 8 5 10  7 9 2 3 5 0 6 8 9 -- 8 8 3 10     Velvetleaf 2 1 4 1 8 2 0 9 1 0 8 0 8 2 7 1 7 0 1 7 3 1 9 0 9 0 0 9 1 2 2     9 -- 8 -- 1 8 Wheat 0 0 3 0 3 0 0 8 0 0 0 0 1 0 7 1 7 0 0 1 0 0 8 0 8 0     0 1 0 0 0 3 -- 2 3 0 6 Wild oat 0 0 3 0 7 0 0 9 0 0 3 0 6 0 9 4 7 0 0 6     0 0 9 2 9 0 0 8 0 0 0 9 -- 10  10       3 9                                     COMPOUND (2000 g/ha)  38 39 40 4     1 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 5758 59 60 61 62 63 64 65 6     6 67 68 6970       Barley 1 0 4 0 -- 3 4 1 6 1 3 1 7 0 0 8 1 6 1 5 0 0 3 7 2 1 0 0 1 0 8     8 0 Barnyardgrass 5 2 7 0 -- 8 9 9 9 4 9 9 9 2 1 9 4 9 9 10  4 4 9 9 7 7     9 9 8 1 9 9 6 Cheatgrass 0 0 2 0 -- 1 6 0 8 0 4 1 6 0 0 4 0 1 2 9 0 0 5     7 1 2 0 2 5 0 9 9 0 Cocklebur 5 1 7 1 -- 8 8 5 8 7 7 7 8 0 5 8 5 3 8 9 3     1 8 8 2 8 6 7 5 0 9 8 3 Corn 4 1 5 0 -- 4 8 5 7 1 5 6 8 0 0 8 1 6 7 7 3     0 4 7 4 2 1 4 6 0 8 7 0 Cotton 9 710  0 -- 10 10 10 10 5 10 10 10 2 8 10     10 10 10 10 7 6 10  10 10 8 9 10  4 0 10  7 6 Crabgrass 8 0 9 0 -- 10 10     9 9 8 9 9 9 5 2 9 3 9 10 10  9 5 10  9 8 9 8 9 10  5 -- 9 3 Giant     Foxtail 9 3 9 2 -- 9 10  8 9 7 9 9 9 9 4 9 5 9 9 10  8 0 9 9 8 6 8 9 9 0     9 9 2 Morningglory 8 3 9 1 -- 9 10  7 8 5 8 7 9 2 5 9 3 8 9 10  5 1 8 9     4 9 7 7 2 1 9 8 2 Nutsedge 0 0 2 0 -- 3 8 3 7 0 5 47 0 0 7 0 5 7 7 1 0     -- 7 3 -- 0 0 0 -- 8 -- 0 Rice 1 0 5 0 -- 1 5 4 8 2 5 4 6 0 0 8 1 3 6 9     1 0 2 8 3 2 0 3 4 0 8 6 0 Sorghum 1 0 4 0 -- 5 7 3 8 2 6 5 9 0 0 8 5 6 8     9 0 0 4 9 4 1 0 3 2 0 8 7 0 Soybean 6 3 7 2 -- 9 9 8 9 2 7 8 8 4 3 9 6 9     9 8 3 1 7 9 5 7 3 4 9 0 9 9 5 Sugar beet 9 3 9 2 -- 10 10 10 9 7 8 8 9 4     5 9 5 9 9 10  7 5 9 9 6 9 8 9 8 0 9 8 3 Velvetleaf 5 1 7 0 -- 6 8 4 8 5     8 7 8 0 1 9 1 6 610  3 0 7 9 7 5 1 7 1 0 7 7 0 Wheat 0 0 1 0 -- 1 4 2 5     2 2 2 7 0 0 8 0 5 1 5 0 0 3 7 1 1 0 2 0 0 5 5 0 Wild oat 4 1 6 0 -- 6 8     2 9 1 8 7 9 0 0 9 3 8 7 9 2 1 7 10       4 7 5 8 5 0 9 8 2                      COMPOUND (2000 g/ha)  71 72 73     74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 94 959697 98 99 1     00 101 102 103 104       Barley 51 9 9 5 5 0 0 1 1 0 6 0 6 0 0 8 0 7 6 1 0 0 1-- 0 2 2 5 4 0 3     2 Barnyardgrass 95 9 9 9 9 1 7 7 6 7 9 4 9 6 0 9 8 8 8 0 0 0 6 --0 9 8 9     9 2 9 7 Cheatgrass 70 9 9 0 7 0 01 0 0 7 0 9 1 0 9 0 5 5 0 0 0 1 --0 5 2     8 3 08 2 Cocklebur 7 5 9 8 6 10  1 2 5 4 2 8 6 9 6 3 9 5 7 7 4 3 1 6 --1     7 8 9 8 7 8 6 Corn 62 10  9 6 7 0 0 1 3 1 4 3 9 3 0 9 6 7 7 2 1 0 4 -- 2     7 7 7 5 2 4 3 Cotton 10 9 10 10 8 10  0 9 7 9 8 10  5 10 10  6 8 5 7 10     10  4 0 10  -- 0 10  9 10  10 6 10  9 Crabgrass 94 10 10 10  10  3 3 9 9     9 9 4 10  -- 1 10  9 9 9 10  5 2 9 -- 5 9 9 10  9 4 9 8 Giant Foxtail 92     10  9 9 9 3 7 8 7 9 9 4 9 9 0 9 9 9 9 7 1 1 5 -- 2 9 9 9 9 1 9 5     Morningglory 10  9 10 10 9 10  1 5 7 7 1 9 6 10  9 5 9 7 10  7 7 3 2 8--     1 7 9 10  7 4 7 4 Nutsedge ---- 9 9 2 3 0 0 0 0 0 1 1 9 2 0 9 5 5 5 0 0     0 3-- 0 3 7 3 8 0 5 -- Rice 31 9 8 3 5 0 0 1 0 1 5 1 10  4 0 9 1 7 6 0 0     0 1-- 0 3 2 4 4 0 3 3 Sorghum 61 9 9 6 7 0 0 1 2 2 6 1 9 1 0 90 6 6 0 0     0 4--0 6 2 7 4 0 5 2 Soybean 10 6 9 9 6 6 1 2 5 5 2 8 4 10 10  4 9 8 8 7     9 7 3 5-- 2 8 8 9 8 5 8 4 Sugar beet 98 10 10  9 10  0 6 9 9 9 10  7 10     10  6 9 8 9 9 7 5 0 8 -- 3 9 10  10  9 7 9 9 Velvetleaf 85 7 5 2 7 2 2 2     1 5 8 5 9 2 2 9 2 7 7 2 2 0 4-- 0 7 8 9 7 1 9 3 Wheat 62 9 9 5 2 0 0 0 0     0 3 0 8 0 0 7 0 4 4 0 0 0 3-- 0 3 3 2 2 0 3 1 Wild oat 10 2 10  9 8 9 0     2 2 5 4 10  1 10       2 0 9 2 6 8 0 0 0 8-- 1 6 4 9 4 2 8 5                    COMPOUND     (2000 g/ha) COMPOUND (400 g/ha)  105 106 107 108 109 110 111 112 113 114 1     15 116 117 1188 15 16 17  18 19 20 21 22 23 24 25 26 27 28 29 30 31 32     33 34       Barley 2 0 3 -- 3 6 1 1 2 -- -- -- 6 95 3 0 2 0 0 0 0 0 6 0 0 0 0 0 0     0 0 0 1 0 Barnyardgrass 8 2 9 -- 9 9 7 7 9 -- -- -- 9 9-- 6 1 -- 0 0 1 0     0 9 0 7 0 0 5 0 1 1 8 3 6 Cheatgrass 2 0 0 -- 6 4 4 2 9 -- -- -- 1 93 3     0 1 0 0 0 0 0 6 0 1 0 0 0 0 0 0 2 5 2 Cocklebur 9 6 5 -- 9 5 6 7 9 -- --     -- 7 98 42 7 0 1 6 2 2 7 1 5 0 0 4 0 2 3 8 5 5 Corn 2 1 2 -- 5 3 6 5 7     -- -- -- 6 8 9 3 1 6 0 0 1 0 07 0 5 0 0 2 0 0 2 5 4 3 Cotton 10  10  9     -- 9 9 9 10  10  -- -- -- 8 10 4 9 4 10  0 0 8 0 0 9 1 9 0 0 -- 0 1 4 4     6 5 Crabgrass 6 4 9 -- 8 9 4 9 10  -- -- -- 9 9-- 9 0 -- 0 0 4 0 0 9 1 9     0 0 5 0 1 5 9 9 9 Giant Foxtail2 1 5 -- 8 4 3 7 9 -- -- -- 9 9 9 5 0 9 0     0 1 0 0 9 0 9 1 0 7 0 3 6 9 9 9 Morningglory 7 1 8 -- 8 8 9 9 9 -- -- --     8 10  8 9 7 7 0 1 2 4 -- 9 2 8 0 1 7 0 2 7 9 8 7 Nutsedge -- 2 0 -- -- 3     1 1 5 -- -- -- 8 9 5 5 0 4 0 0 -- 0 0 5 0 6 1 0 0 0 0 0 3 2 2 Rice 3 0 1     -- 7 2 3 2 8 -- -- -- 7 9 7 3 0 5 0 0 0 0 0 7 0 3 -- 0 0 0 0 0 2 1 1     Sorghum 2 0 1 -- 8 3 1 2 5 -- -- -- 5 10  7 2 0 4 0 0 1 0 0 4 0 3 0 0 1     0 0 0 7 2 4 Soybean 6 4 5 -- 8 7 8 8 9 -- -- -- 8 9 9 9 8 9 0 5 7 5 2 9     3 7 0 3 7 1 5 5 9 8 10  Sugar beet 9 6 10  -- 9 9 10  9 10  -- -- -- 8     10  9 9 6 9 0 3 5 5 3 8 4 9 3 1 1 0 2 5 8 8 8 Velvetleaf 8 1 6 -- 7 5 7     4 9 -- -- -- 7 9 7 4 0 5 0 1 4 -- 2 -- 0 7 0 0 2 0 1 -- 8 7 7 Wheat 2 0     3 -- 3 3 0 1 1 -- -- -- 1 9 1 4 0 1 0 0 0 0 0 4 0 2 0 0 0 0 0 0 0 1 0     Wild oat 6 2 5 -- 7 9 3 5 7 -- -- -- 4 10 8 6 1 6 0 0 2 0 0 8 0 7 0 0 2     0 0 0 7 2 4       COMPOUND (400 g/ha)  35 36 37 38 39 40 41 42 43 44 45 4647 48 49 50 51 5     2 53 54 55 56 57 58 59 60 61 62  63 64 65 66 67 68 69 70       Barley 2 0 0 1 0 00 1 0 1 0 2 0 2 0 2 0 0 3 0 2 0 3 0 0 1 6 1 0 0 1 0     0 4 3 0 Barnyardgrass 9 3 8 2 0 3 0 4 3 6 4 9 0 9 9 8 0 2 9 4 7 8 9 0 1     7 9 5 5 0 7 2 0 9 9 2 Cheatgrass 4 0 0 0 0 1 0 00 2 0 1 0 2 0 3 0 0 2 0     0 0 5 0 0 1 1 0 0 0 0 0 0 8 3 0 Cocklebur 8 4 6 3 1 6 0 7 5 5 3 5 5 7 6     5 1 2 7 2 5 7 8 0 1 7 7 4 5 0 5 5 0 8 8 2 Corn 3 2 4 1 0 4 0 2 2 4 1 5 1     4 1 3 0 0 6 0 3 4 4 0 0 1 5 2 1 0 1 1 0 7 7 1 Cotton 10  5 9 7 2 8 0 10     10  9 8 10  5 10  7 10  0 -- 10 10 10  9 10  3 7 10  10  9 9 5 9 3 0 4 8     -- Crabgrass 9 3 9 5 0 7 0 6 9 9 8 10  3 9 9 8 0 0 8 4 8 8 10  0 2 89 9     4 1 8 5 0 9 9 2 Giant Foxtail 9 5 9 5 0 9 0 88 9 5 9 2 9 9 9 3 2 9 6 9 8     9 0 0 5 9 8 2 0 6 6 0 9 9 2 Morningglory 8 6 9 7 1 7 1 86 10  8 7 2 7 7     8 1 2 7 2 7 8 10  1 1 7 8 1 4 2 5 2 1 8 8 4 Nutsedge 1 0 2 0 0 0 0 00 3     1 -- 0 0 3 -- 0 0 4 0 2 3 3 0 0 0 30 -- 0 0 0 -- 3 0 0 Rice 1 0 2 1 0 1     0 0 0 3 2 2 1 4 1 2 0 0 3 0 2 1 7 0 0 3 5 0 0 0 1 0 0 8 3 0 Sorghum 4 0     2 1 0 1 0 2 1 2 1 7 0 5 4 5 0 0 6 1 5 4 5 0 0 4 8 0 0 0 1 0 0 7 5 0     Soybean 10  4 8 5 1 6 0 6 7 9 8 8 1 6 6 8 2 3 9 2 8 9 8 2 1 5 9 2 7 1 5     6 0 9 10  3 Sugar beet 8 2 9 5 1 8 1 8 8 9 8 9 3 9 7 8 1 2 9 5 8 8 10  3     2 8 9 8 7 2 6 6 0 9 8 6 Velvetleaf 7 1 7 1 0 5 0 5 2 7 2 7 3 7 6 5 0 1 6     1 5 4 8 0 0 5 8 4 2 0 5 2 0 2 2 0 Wheat 1 0 0 0 0 0 0 00 2 0 2 0 1 0 1 0     0 3 0 1 0 2 0 0 1 2 0 0 0 2 0 0 2 4 0 Wild oat 5 3 6 3 0 3 0 3 2 3 2 7 1     8 7 8 0 0 8 1 6 4 6 0 0 5 8 3 3 0 6 2 0 7 9 2       COMPOUND (400 g/ha)  71 72 73 7475 76 77 78 79 80 81 82 83 84 85 86 87 8     8 89 90 91 92 94 95 96 97 98 99 100 101 102 103 104 105 106 107       Barley 4 0 6 5-- 2 0 0 0 0 0 1 0 3 0 0 5 0 2 1 0 0 0 0 0 0 1 0 2 -- 0     4 2 00 3 Barnyardgrass 8 5 9 9-- 9 0 5 3 1 4 9 3 9 1 0 9 0 6 7 0 0 0 5 0     0 3 1 7 -- 1 4 2 7 0 3 Cheatgrass 4 0 5 0 -- 2 0 0 0 0 0 2 0 7 0 0 3 0 4     0 0 0 0 0 0 0 2 0 6 -- 0 7 0 0 0 2 Cocklebur 5 3 6 7 -- 7 0 2 4 0 1 5 5     8 3 2 8 2 7 7 3 2 0 7 2 0 6 5 6 -- 1 6 6 7 1 3 Corn 3 1 8 8-- 4 0 0 1 1     0 3 0 7 1 0 7 0 7 5 0 0 0 3 0 0 4 3 3 -- 0 2 1 1 1 2 Cotton 10  5 10  9     -- 10  0 2 5 1 1 10  5 10  8 5 8 2 10  9 4 4 0 8 3 0 9 8 0 -- 3 8 9 10     6 8 Crabgrass 8 2 10  9-- -- 0 2 2 1 7 10  2 9 --  1 9 0 8 7 2 3 0 7 1 0     5 5 7 -- 0 9 1 40 7 Giant Foxtail 3 1 9 9 -- 9 0 5 3 1 2 9 2 9 2 0 9 0 9     8 0 0 0 3 1 0 4 0 3 -- 0 3 0 0 0 2 Morningglory 10  3 10  7 -- 9 0 2 4 1     0 10  4 9 8 3 9 5 7 6 2 2 1 6 2 1 7 8 9 -- 2 5 4 4 1 5 Nutsedge 3 5 7 5     -- 1 0 0 0 0 0 -- 0 6 0 0 -- 0 4 3 0 0 0 0 0 0 0 0 2 -- 0 1 0 0 -- 0     Rice 0 1 7 5 -- 3 0 0 0 0 0 3 0 9 0 0 7 0 5 2 0 0 0 0 1 0 3 0 2 -- 0 1 0     2 0 1 Sorghum 1 1 7 6 -- 6 0 0 0 0 0 3 0 8 1 0 7 0 5 3 0 0 0 3 0 0 1 0 2     -- 0 1 0 1 0 2 Soybean 9 4 9 9 -- 4 0 1 3 1 2 5 2 9 5 2 9 7 6 6 6 3 1 6     2 2 8 7 7 -- 3 8 4 4 2 5 Sugar beet 6 7 9 9 -- 10  0 1 6 1 3 10  5 10  9     2 9 4 8 8 4 2 0 7 3 1 9 8 9 -- 3 8 9 8 5 9 Velvetleaf 3 1 5 2 -- 6 0 1 1     0 0 7 2 9 2 1 7 1 6 5 1 1 0 2 1 0 7 5 7 -- 0 9 2 5 1 2 Wheat 1 0 2 7 --     1 0 0 0 0 0 2 0 1 0 0 3 0 4 1 0 0 0 1 1 0 1 0 1 -- 0 0 0 0 0 0 Wild oat     8 3 7 8 -- 8 0 0 2 0 2 7 0 9 0 0 7 0 6 5 0 0 0 5 1 0 3 3 6 -- 0 5 2 3 0     5  COMPOUND (400 g/ha)  108 109 110 111 112 113 114 115 116 117 118       Barley 0 2 3 0 0 0 -- -- -- 2 9 Barnyardgrass 0 3 6 2 3 3 -- -- -- 9 9     Cheatgrass 0 0 2 1 1 5 -- ---- 1 9 Cocklebur 0 2 3 5 7 8 ------ 7 9 Corn     0 1 1 1 2 2 ------3 7 Cotton 0 8 9 9 9 8 ------7 10  Crabgrass 0 1 3 2 9     9 ------9 10  Giant Foxtail 0 2 1 1 6 8 ------ 9 9 Morningglory 0 4 3 8     7 8 ------ 3 10  Nutsedge -- 0 0 0 0 2 ------1 -- Rice 0 1 0 0 1 2     ------ 2 7 Sorghum 0 1 2 0 1 0 ------1 9 Soybean 0 7 6 7 7 8 ------ 9 9     Sugar beet 0 7 6 7 9 9 ------ 7 10  Velvetleaf 0 1 3 2 6 5 ------ 4 9     Wheat 0 0 0 0 0 0 ------ 0 4 Wild oat 0 1 5 1 2 3 ------ 2 9       PREEMERGENCE COMPOUND (2000 g/ha)  1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 1     6 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33       Barley -- -- 0 0 9 0 0 8 0 0 8 0 8 0 7 4 7 0 0 0 0 0 7 1 8 1 1 2 0 1 2     6 --  Barnyardgrass 9 8 9 0 9 0 0 10  7 0 10  0 10  0 10  9 10  0 8 10     4 0 10  5 10  5 1 10  0 9 9 10  -- Cheatgrass 5 2 7 0 3 0 0 9 2 0 8 0 10      0 9 2 9 0 0 3 0 0 9 1 7 2 0 2 0 0 0 9 -- Cocklebur 2 3 0 0 0 0 2 8 1 0     3 0 6 0 5 2 4 0 0 0 1 0 2 3 1 0 1 4 0 0 4 5 -- Corn 4 6 5 0 9 0 0 9 4 0     8 0 7 0 7 5 7 0 0 2 0 0 8 6 7 2 4 9 0 0 6 8 -- Cotton 0 0 0 0 2 0 0 6 0     0 0 0 0 0 7 2 5 0 0 0 0 0 9 2 3 0 0 2 0 0 0 0 -- Crabgrass 9 8 10  3 9 8     0 10  9 0 10  0 10  0 10  10  10  3 9 10  9 5 9 8 10  9 9 10  0 9 9 9 --     Giant Foxtail -- -- 10  3 9 2 0 10  10  0 10  5 10  0 10  10  10  0 10     8 10  6 10  9 10  9 9 10  0 8 8 10  -- Morningglory 9 10  10  0 10  8 8     10  10  0 10  1 10  1 10  10  10  0 9 7 10  8 10 10 10 2 9 8 0 9 10 10     -- Nutsedge 2 3 0 0 3 0 0 7 4 0 5 0 9 -- 8 -- 3 0 0 0 0 0 6 2 4 0 0 3 0     0 7 5 -- Rice 2 3 7 0 5 0 0 9 1 0 5 0 4 0 6 5 7 0 0 4 0 0 8 3 6 0 0 5 0     0 5 4 -- Sorghum 1 2 7 0 9 0 0 10  3 0 9 0 10  0 8 6 9 0 0 5 0 0 10  5 9     2 1 7 0 0 7 9 -- Soybean 5 7 9 0 9 0 0 9 8 3 8 1 9 2 9 9 8 0 8 8 8 8 9 8     8 1 7 9 0 8 8 8 -- Sugar beet 5 10  10  0 10  3 4 10  10  0 10  5 10  0     10  9 10  0 9 10  9 8 10 10 10 2 8 10  0 9 9 10  -- Velvetleaf 2 4 10  0     10  6 1 10  9 0 7 0 10  0 10  9 10  0 5 10  7 3 10  9 10  0 0 7 0 2 8 10      -- Wheat 1 0 2 0 5 0 0 9 0 0 5 0 3 0 6 3 7 0 0 1 0 0 8 0 5 2 1 0 0 0 0     1 -- Wild oat 8 2 7 0 6 0 0 9 1 0 7 0 10  0 10  3 10  0 0 7 0 0 9 2 10     0 2 4 0 3 2 9 --       COMPOUND (2000 g/ha)  34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49     50 51 52 53 54 55 56 57 58 59 60 61 62 63       Barley 2 9 7 5 0 0 4 0 -- 2 6 0 7 0 6 0 9 3 0 9 1 8 2 9 0 0 3 9 1 1     Barnyardgrass 10  10  10  10  9 09 1 -- 9 10  9 10  0 10 10 10 9 5 10  8     10 10 10  9 6 10 10  7 8 Cheatgrass 4 10  8 9 2 0 5 0 -- 7 6 2 9 0 10  2     9 5 3 10  2 10 10 10  0 0 7 10  4 3 Cocklebur 3 3 1 1 0 0 2 0 -- 2 6 0     -- -- 3 7 5 3 1 8 0 1 6 5 0 0 2 9 3 2 Corn 5 7 4 6 0 0 4 0 -- 5 5 1 8 0     4 4 9 3 0 9 2 7 8 8 5 0 2 9 0 2 Cotton 1 9 6 9 0 7 8 0 -- 4 5 4 1 0 8 1     10  6 3 8 0 5 10  8 0 0 -- 7 2 9 Crabgrass 10 10 10 10 10 2 10  8 -- 10     10 10 10  5 7 10  9 9 9 9 9 10 10 10  10  9 10  9 10 10  Giant Foxtail     10 10  9 10  9 710  9 -- 10 10 10 10 4 7 10 10  9 8 10  9 10 10 10  10     9 10  9 9 10  Morningglory 10 10 10  9 9 0 7 1 -- 9 10 10  9 5 10 10 10     10  5 10  6 10 10 10  10  5 10 10  9 6 Nutsedge 1 1 2 7 2 0 1 0 -- 0 8 0     0 0 0 5 7 4 0 6 0 0 7 4 1 0 0 5 2 1 Rice 1 5 2 6 0 0 5 0 -- 1 4 2 1 5 2     3 7 5 0 7 0 6 9 9 2 0 3 7 2 0 Sorghum 9 8 7 8 5 14 0 -- 9 8 4 9 5 7 7 9     3 0 10  3 8 9 10  3 0 7 9 4 3 Soybean 8 7 7 5 1 0 5 0 -- 7 8 8 4 4 6 8 9     8 0 9 1 7 10  8 8 0 2 8 6 0 Sugar beet 10 10 10 10 10 0 10  0 -- 9 10 10     10  9 10 10 10 10  0 10  7 10 10 10  10  5 10 10 10  9 Velvetleaf 10 10     10 10 7 0 9 0 -- 9 10 10 10  0 10  8 10  7 2 10  4 10 10 10  10  3 9 10     10  6 Wheat 1 4 3 5 0 0 1 0 -- 3 2 1 7 0 2 0 9 1 0 7 0 6 9 9 1 0 2 9 1 0     Wild oat 4 10  7 9 1 0 9 0 -- 8 7 4 9 1 9 2 9 2 0 9 7 9 8 10  3 0 10 10     2 8       COMPOUND (2000 g/ha)  64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79     80 81 82 83 84 85 86 87 88 89 90 91 92 94 95 96       Barley 1 3 2 0 9 6 0 9 0 9 6 4 5 0 0 0 2 0 7 0 6 0 0 8 1 2 3 0 0 0 4--     Barnyardgrass 9 9 8 0 10  9 3 10  5 10 10 9 9 3 3 8 9 7 10  3 10  9 0 10     10  8 9 4 0 0 8 -- Cheatgrass 5 4 7 0 10  9 3 10  4 9 9 0 8 0 0 2 1 0 9     3 10  2 0 10  0 5 5 0 0 0 6 -- Cocklebur 2 3 1 0 7 8 0 0 0 8 9 1 5 0 0     -- 1 7 0 0 7 2 0 5 3 6 2 1 4 0 1 -- Corn 0 2 6 0 8 6 1 7 0 9 7 6 5 0 0 2     3 1 3 0 7 3 0 9 7 7 4 3 0 0 2 -- Cotton 1 9 0 0 3 8 0 9 1 10 10  0 8 0 0     1 0 0 1 0 10  1 1 9 -- 2 6 -- 0 0 2 -- Crabgrass 9 9 9 4 10 10  8 10  5     10 10 10  10  7 9 10  9 10 10  5 10  9 4 10 10 10 10  9 7 8 9 -- Giant     Foxtail 10 10  9 5 9 9 6 10  5 10 10 10  10  9 9 10 10  9 10  4 10 10  2     10 10  9 9 10  8 9 10  -- Morningglory 9 10 10  1 10 10  8 10  7 10 10     9 9 0 0 8 10  3 10  2 10 10  6 10 10 10 10 10 0 0 8 -- Nutsedge 0 3 0 0     5 1 0 3 0 5 6 3 2 0 0 2 0 0 1 0 5 3 0 5 5 5 -- 1 0 0 10  -- Rice 0 4 1 0     6 2 0 5 1 8 7 1 0 0 0 1 2 0 3 0 6 2 0 8 4 5 4 2 0 0 1 -- Sorghum 2 5 4 0     10  8 2 9 1 10 10  7 8 0 0 3 1 5 7 1 8 5 0 10  7 8 7 3 0 0 7 -- Soybean     1 4 8 0 9 7 1 8 1 9 9 6 3 0 0 0 7 0 3 0 8 8 2 9 8 7 7 9 0 0 5 -- Sugar     beet 10  8 10  0 10 10  5 10  7 10 10 10 10  0 0 8 9 6 10  5 10 10 10 10     10 10 10  9 0 0 9-- Velvetleaf 9 9 8 0 10 10  2 10  7 10 10 10  10  0 2     4 8 0 10  0 10  5 5 10 10 10 10 10 1 0 3 -- Wheat 0 1 0 0 7 3 0 7 0 10     7 1 5 0 0 0 1 0 4 0 7 0 0 9 0 3 5 0 0 0 0 -- Wild oat 6 6 5 0 9 9 0 10     0 10 10 8 9 0 2 3 4 2 8 0 10       2 1 9 2 6 7 3 0 0 5 --                       COMPOUND (2000 g/ha)     COMPOUND (400 g/ha)  97 98 99 100 101 102 103 104 105 106 107 108 109     110 111 112 113 114 115 116 117 118 8 15 16 17 18 19 20 21 22       Barley 0 4 4 7 5 0 5 0 2 0 7 -- 7 9 1 5 2 -- -- -- 2 9 6 4 0 2 0 0 0 0     0 Barnyardgrass 0 10  9 10  10  5 10  9 9 8 10  -- 10 10 10  9 10  -- --     -- 10 10  10  9 2 9 0 0 4 0 0 Cheatgrass 0 5 7 9 8 2 10  4 6 0 9 -- 9 10      1 8 6 -- -- -- 5 10  2 1 0 1 0 0 0 0 0 Cocklebur 0 1 0 2 2 1 2 0 2 0 0     -- 9 8 5 1 10  -- -- -- 6 10  1 0 0 -- 0 0 0 0 0 Corn 0 5 2 3 5 1 3 1 1     4 5 -- 6 6 2 5 7 -- -- -- 6 7 7 3 2 2 0 0 1 0 0 Cotton 0 1 1 8 1 0 9 1     -- 0 1 -- 8 10  1 0 1 -- -- -- 0 10  0 0 0 1 0 0 0 0 0 Crabgrass 6 10 10     10 10 10 10 10 10  8 10  -- 10 10 10 10 10 -- -- -- 9 10  10 10  9 10  0     5 8 8 0 Giant Foxtail 4 10 10 10 10 10 10 10 10 9 10  -- 10  10 10 10 10      -- -- -- 10 10  10 10 10 10 0 1 2 7 0 Morningglory 5 10 10 10 10 10  9     9 8 4 8 -- 10 10 10 10 10  -- -- -- 10 10  10 10  8 9 0 0 5 1 3 Nutsedge     0 0 1 2 3 2 1 0 0 0 2 -- 10  2 5 0 3 -- -- -- 5 3 4 0 0 1 0 0 0 0 0 Rice     0 5 1 1 6 0 0 2 2 0 1 -- 7 6 5 4 4 -- -- -- 4 7 7 5 0 3 0 0 0 0 0     Sorghum 0 7 8 7 7 4 7 3 5 0 7 -- 8 8 5 5 10  -- -- -- 9 98 5 0 7 0 0 0 0     0 Soybean 7 8 6 8 8 7 7 2 2 0 4 -- 9 7 9 5 9 -- -- -- 9 9 9 4 2 2 0 3 2     2 1 Sugar beet 9 10 10 10 10 10 10 10 10  9 10  -- 10 10 10 10 10  -- --     -- 10 10  9 10  8 9 0 2 4 0 1 Velvetleaf 1 10  9 10 10  7 9 10  7 6 10     -- 10 10 10  8 10  -- -- -- 10 10  10 10  0 8 0 0 6 1 0 Wheat 0 1 1 3 3     0 5 0 0 0 1 -- 4 6 0 5 2 -- -- -- 7 10  5 3 0 2 0 0 0 0 0 Wild oat 0 7 8     9 8 0 10  5 6 0 9 -- 9 10  2 7 7 -- -- -- 9 10       6 3 0 5 0 0 1 0 0          COMPOUND (400 g/ha)  23 24 25 26 27 28 29     30 31 32  33 34 35 36 37 38 39 40 41 4243 44 45 46 47 48 49 50 51 52 53     54 55       Barley1 0 2 0 0 00 0 0 4 1 0 6 1 3 0 0 1 0 0 0 1 0 6 0 3 0 7 0 0 7 0 6     Barnyardgrass 10  0 9 0 0 9 0 1 2 9 9 9 9 7 10  4 0 8 0 5 9 9 2 10  0 10      7 9 2 310  3 9 Cheatgrass 5 0 3 0 0 0 0 0 0 3 3 0 5 0 7 0 0 2 0 6 1 0 0     7 0 6 0 7 2 0 9 0 5 Cocklebur 0 0 0 0 0 1 0 0 0 2 2 00 0 0 0 0 0 0 00 2     2 -- 0 3 0 0 0 0 2 0 0 Corn 5 0 6 0 0 1 0 0 2 5 3 1 3 0 1 0 0 1 0 0 2 3     0 3 0 2 3 8 0 0 8 0 6 Cotton 3 0 0 0 0 -- 0 0 0 0 1 0 3 1 0 0 0 5 0 0 1     0 0 -- 0 4 0 0 1 0 3 0 0 Crabgrass 9 5 10  6 0 9 0 5 8 9 9 9 10  10 10     9 0 9 3 810 10 10 10 2 10 10  9 9 8 9 5 9 Giant Foxtail 10  8 10  7 4 10      0 5 4 9 10  9 10  9 10  9 1 10  7 9 9 10 10 10  2 10  9 10  8 8 10  5     10  Morningglory 10  3 10  0 0 5 0 3 3 10  8 6 9 10  8 7 0 7 0 78 10 10     10  0 8 9 10  3 1 10  0 10  Nutsedge 3 0 0 0 0 0 0 0 0 2 1 0 0 0 4 -- 0     0 0 0 0 1 0 0 0 0 1 3 0 0 3 0 0 Rice 5 0 5 0 0 0 0 0 1 1 0 0 1 -- 1 0 0     2 0 1 1 1 1 0 2 0 0 2 0 0 5 0 4 Sorghum 8 0 5 0 0 3 0 0 2 8 3 4 6 1 6 0     0 2 0 56 2 0 8 1 3 3 8 0 0 8 0 7 Soybean 8 5 4 0 0 3 0 0 6 7 2 3 7 3 1 0     0 2 0 0 5 6 7 3 0 2 2 4 0 0 5 0 3 Sugar beet 10  8 10  0 0 5 0 0 0 8 10     10 10  6 9 1 0 10  0 22 10  8 10  6 10  9 9 7 0 10  0 10  Velvetleaf 10     1 7 0 0 2 0 0 0 8 5 8 9 4 7 0 0 5 0 6 7 10  9 9 0 10  0 10  2 0 10  0 8     Wheat 3 0 1 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0 0 00 0 0 2 0 0 0 6 0 0 2 0 1     Wild oat 9 0 7 0 0 0 0 1 0 6 4 0 9 1 5 0 0 5 0 0 0 3 0 7 0 8 0 8 0 0 8 0     7       COMPOUND (400 g/ha)  56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71     72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 8788       Barley0 6 0 0 2 7 0 0 0 0 0 0 3 4 0 3 0 5 4 -- 3 0 0 0 0 0 3 0 4 0 0 2     0 Barnyardgrass 10  10  0 0 8 10  4 8 1 8 2 0 9 9 2 10  3 10 10  --  9 0     0 5 3 1 9 0 10  1 0 10  2 Cheatgrass 0 9 0 0 7 8 0 2 2 1 1 0 7 8 0 10  0     4 8-- 5 0 0 0 0 0 5 0 8 0 0 3 0 Cocklebur 3 2 0 0 0 2 -- 0 0 -- 0 0 5 5     0 0 1 2 2-- 5 0 0 0 0 0 0 0 1 0 0 0 0 Corn 5 4 0 0 1 4 1 1 1 0 3 0 5 4 1     4 0 6 6 -- 2 0 0 1 0 0 2 0 5 0 0 7 0 Cotton 1 0 0 0 0 4 1 0 0 -- 0 0 2     10  0 2 0 9 3-- 6 0 0 0 0 0 0 0 3 0 0 30 Crabgrass 10  10  9 5 10  9 9     10  9 9 -- 1 10 10  9 10  1 10 10  --10  2 6 9 9 9 10  0 10  3 2 10  9     Giant Foxtail10 10  8 1 9 10  8 10  9 -- 8 2 9 9 4 10  1 10 10  -- 10  3     6 9 9 9 10  0 10  2 0 9 10  Morningglory 10  8 5 0 9 9 3 5 0 7 5 0 10  9     5 9 3 10 10  -- 8 0 0 2 2 0 7 0 10  9 1 10  6 Nutsedge -- 0 0 0 0 3 0 0     0 0 0 0 2 0 0 1 0 3 2 -- 0 0 0 0 0 0 0 0 4 0 0 3 0 Rice 1 4 0 0 0 2 1 0     0 0 0 0 2 3 0 4 0 6 3-- 0 0 0 0 0 0 0 0 3 0 0 4 1 Sorghum 2 7 0 0 7 7 3     2 1 2 1 0 8 8 0 6 0 8 7 -- 5 0 0 1 0 0 7 0 8 0 0 8 0 Soybean 8 6 2 0 0 7     4 0 0 1 1 0 7 7 0 1 0 8 9 -- 4 0 0 0 1 0 0 0 6 2 2 7 4 Sugar beet 10 10     3 0 9 10 10  8 5 5 6 010 10  3 6 4 10 10  -- 9 0 0 0 0 7 10  0 10  5 3     10  9 Velvetleaf 10  9 4 0 5 10  5 6 0 3 1 0 9 9 3 10  5 10  7 -- 7 0 0     0 3 0 7 0 10  0 2 10  0 Wheat 0 3 0 0 0 4 0 0 0 0 0 0 2 2 0 5 0 5 1 -- 0     0 0 0 0 0 1 0 1 0 0 3 0 Wild oat 2 10  0 0 6 9 2 3 0 2 2 0 7 9 0 10  0 4     3 -- 6 0 0 0 0 0 9 0 10       0 0 5 0                                           COMPOUND (400 g/ha)  8     9 90 91  92 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109     110 111 112 113 114 115 116 117 118       Barley 2 0 0 0 0 2 0 0 0 1 3 -- 0 4 0 0 0 1 0 2 3 0 0 0 -- -- -- 0 9     Barnyardgrass 8 5 0 0 0 5 0 0 7 5 9 -- 0 9 7 5 2 9 0 9 9 1 910  -- -- --     8 10 Cheatgrass 1 0 0 0 0 4 0 0 2 0 5 -- 0 7 0 30 2 0 0 10  0 1 2 -- --     -- 0 10  Cocklebur 1 1 0 0 0 0 0 1 1 0 -- -- 0 1 0 00 0 0 2 2 0 0 1 --     -- -- 1 7 Corn 6 1 0 0 0 1 0 0 2 2 2 -- 0 1 1 0 0 0 0 2 2 0 1 2 -- -- --     1 8 Cotton 9 0 0 0 0 0 0 0 0 0 1 -- 0 1 0 00 0 0 1 8 0 0 1 -- -- -- 0 4     Crabgrass 10  10  8 -- 0 10  0 1 9 910  -- 7 10 10 10  7 10  9 10  10  9     9 10  -- -- -- 9 10  Giant Foxtail 9 9 6 2 0 10  0 0 10  8 10  -- 5 10     9 8 6 10  0 9 10  9 10  9 -- -- -- 9 10  Morningglory 9 10  3 0 0 8 0 0     9 7 9 -- -- 10  0 4 0 0 0 8 9 10  8 10  -- -- -- 10 10  Nutsedge 0 0 0 0     0 2 0 0 0 0 -- -- 0 0 0 0 0 0 0 0 0 0 0 2 -- -- -- 0 2 Rice 3 0 0 0 0 0     0 0 0 1 1 -- 0 0 0 00 0 0 1 2 -- 0 2 -- -- -- 0 4 Sorghum 7 1 0 0 0 7 0     0 2 2 7 -- 0 5 1 20 1 0 5 5 0 1 6 -- -- -- 2 8 Soybean 3 1 2 0 0 1 0 0 5     1 4 -- 0 2 1 0 0 0 0 2 2 5 2 3 -- -- -- 7 9 Sugar beet 10 10  4 0 0 9 0     3 10  7 9 -- 7 9 9 76 9 0 10  9 9 10 10  -- -- -- 10 10  Velvetleaf 10     10  3 0 0 1 0 0 7 6 7 -- 0 9 8 50 5 0 7 10  8 7 9 -- -- -- 9 10  Wheat 0     1 0 0 0 1 0 0 0 0 0 -- 0 2 0 0 0 0 0 0 1 0 0 0 -- -- -- 0 4 Wild oat 4 5     0 0 0 4 0 0 1 0 9 -- 0 8 2 20 4 0 5 9 0 1 2 -- -- -- 0 10     (Compound 89 tested at 1000 grams/ha.)

TEST B

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellariamedia), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromustectorum), giant foxtail (Setaria faberi), green foxtail (Setariaviridis), jimsonweed (Datura stramonium), johnsongrass (Sorghumhalepense), lambsquarters (Chenopodium album), morningglory (Ipomoeaspp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassiaobtusifolia), soybean (Glycine max), sugar beet (Beta vulgaris), teaweed(Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Triticumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus), tubers were planted andtreated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to eighteen cm (two to three leaf stage) forpostemergence treatments. Treated plants and controls were maintained ina greenhouse for approximately 24 days, after which all species werecompared to controls and visually evaluated. Preemergence andpostemergence application rates for each compound are listed in Table B.Plant response ratings, summarized in Table B, are based on a scale of 0to 10 where 0 is no effect and 10 is complete control. A dash (-)response means no test result.

    TABLE B      COMPOUND (1000 g/ha) (500 g/ha) 3 5 9 13 28 43 44 45 75 104 3 5 8 9 13     15 16 17 23 25 28 33 34 35 36 37 40 43 44 45       POSTEMERGENCE Barley 3 3 0 4 2 0 4 0 3 0 2 2 6 0 2 2 0 2 6 3 0 1 0 3 5 5      1  0  3  0 Barnyardgrass 0 10 0 10 10 10 10 5 10 1 0 10 9 0 9 10 0 7 10     10 2 10 4 10 10 10 4 10  7  3 Blackgrass 5 9 0 10 7 10 10 3 10 3 2 6 10     0 5 10 4 10 10 10 5 3 5 8 5 9 1  7  9  0 Chickweed3 9 5 10 3 8 10 5 10     102 7 9 3 6 9 3 10 10 10 2 7 10 10 10 10 10  7  7  3 Cocklebur3 5 0 3 2     6 5 0 8 82 3 6 0 0 2 0 5 6 5 2 5 6 6 7 8 6  5  3  0 Corn0 0 0 4 4 3 3 0     3 2 0 0 6 0 2 5 0 2 5 4 2 0 0 3 8 4 2  3  0  0 Cotton8 8 2 7 -- 4 4 3 --     8 5 4 2 0 5 8 2 5 5 4 0 3 0 10 5 8 7  3  4  3 Crabgrass0 4 0 10 10 10 10     9 10 1 0 -- 8 0 4 10 7 7 10 10 3 9 5 10 10 10 9 10 10  6 Downy brome0 5     0 5 3 0 6 0 0 4 0 3 3 0 0 4 0 3 8 3 0 0 2 3 3 0 0  0  4  0 Giant     foxtail0 4 0 1010-- 10 6 10 1 0 3 10 0 9 10 2 3 10 10 8 10 0 10 10 10 6     --  7  0 Green foxtail0 4 0 9 10 6 10 7 9 1 0 0 9 0 6 10 0 5 10 9 7 8 4     10 10 9 5  6 10  0 Jimsonweed9 10 4 101010101010107 10 8 3 10 10 2 7 10     10 8 10 8 10 10 10 10 10 10  7 Johnsongrass3 4 0 7 3 1010 0 8 40 3 6 0 4     5 0 0 8 8 2 10 0 8 10 9 3 --  5  0 Lambsquarters8 10 8 1010101010 9 10 8     9 9 7 10 10 7 9 10 10 10 1010101010101010  9 Morningglory6 8 5 10 8 5 10     7 8 9 5 4 -- 3 10 8 7 9 5 8 2 5 1 9 10 6 5  5 10  3 Nutsedge 0 0 9 4 5 6     -- -- 0 0 0 0 7 6 0 2 0 4 8 7 2 3 2 0 1 0 0  0 -- -- Rape 6 10 3 10 7 10     10 5 9 9 4 9 10 0 10 1010101010 3 7 9 101010 9 1010  4 Rice0 1 0 4 3 3 5     3 4 1 0 0 4 0 3 3 0 4 7 4 2 0 0 4 8 5 3  0  4  0 Sicklepod2 6 0 4 9 3 7     -- 9 70 -- 5 0 0 6 3 5 10 5 5 6 0 8 10 5 9 --  6  6 Soybean5 6 3 10 5     1010 0 -- 6 5 5 8 2 9 10 5 5 8 10 3 4 5 4 10 10 5  8  7  0 Sugar beet5     10 9 10 5 10101010104 1010 8 1010 7 101010 2 101010101010101010 Teaweed0     4 0 7 5 5 8 5 2 -- 0 -- 3 0 4 7 4 7 10 7 2 5 5 6 4 10 4  3  7  4     Velvetleaf6 -- 3 4 -- 7 6 3 6 8 2 6 8 0 2 7 5 6 9 9 8 3 0 4 5 7 6  6  4     2 Wheat 0 1 0 0 0 0 0 0 2 0 0 0 1 0 0 1 1 1 2 0 0 0 0 0 3 1 0  0  0  0     Wild buckwheat 8 10 7 10 5 1010 -- 10 8 3 9 9 0 7 -- -- 8 1010 2 10 7 9     1010101010 3 Wild Oat0 5 0 7 3 5 8 0 5 4 0 3 6 0 3 7 3 4 8 5 2 0 2 3 5 3     1  5  3      0     COMPOUND (500 g/ha) (250 g/ha) 46 48 53 55 56 57 61 68 69 71 73 74 75 76 8     2 84 87 90 104 107 117 3 5 8 13 15 16 17 23       POSTEMERGENCE Barley 4 1 4 3 0 5 5 3 3 3 6 4 0 3 3 7 7 2  0  3  3 0 0     3 0 2 0 1 4 Barnyardgrass 5 10 10 10 0 10 -- 8 7 10 10 10 8 4 3 10 9 6     1 --  9 0 4 9 5 10 0 7 5 Blackgrass 10 610 -- 6 10 8 10 7 10 10 10 7 --     8 10 10 7  1  5  10 0 2 5 3 9 2 5 10 Chickweed 9 9 10 10 5 10 7 10 7 10     10 10 1010 8 1010 9  9  9  10 0 4 7 3 7 0 8 10 Cocklebur 6 6 8 8 3 7 --     -- -- 7 3 4 7 9 3 10 3 5  8 --  2 0 2 4 0 0 0 3 5 Corn 6 6 5 3 0 4 -- 3     3 5 8 5 3 2 3 7 6 5  1  3  4 00 3 0 3 0 2 2 Cotton 5 8 10 8 8 10 -- 8 7     10 8 5 3 7 3 10 9 3  7  4  6 4 2 1 3 5 0 3 3 Crabgrass 6 10 10108 10 --     10101010101010101010 7  1  8  7 00 7 0 9 5 4 9 Downy brome 3 0 1 0 0 7 4     3 2 6 8 9 0 4 3 7 6 2  0  1  2 00 2 0 3 0 2 5 Giant foxtail 10 9 -- --     1010 -- 8 6 9 9 10 8 3 10 10 9 3  1  5  10 0 0 5 0 8 0 2 10 Green     foxtail 7 10 1010 9 10 -- 9 7 10 8 10 9 6 6 10 9 6  0  4  5 0 0 9 0 9 0     3 10 Jimsonweed 10 10 1010 9 10 -- 101010101010 8 1010107   10 --  10 5     8 6 9 10 -- 2 10 Johnsongrass 9 8 10 9 0 9 -- 7 5 8 8 7 5 4 7 10 9 3  1     3  7 0 0 2 0 4 00 4 Lambsquarters 10 10 10109 10 -- 1010101010 --     10101010 5  10  10  8 8 8 8 9 10 7 7 9 Morningglory 7 67 7 8 10 -- 8 7     10 9 9 4 8 5 1010 8  8  8  3 3 4 9 9 7 7 3 2 Nutsedge 5 0 4 -- -- -- --     7 3 0 7 7 0 3 0 6 3 3  0  5 -- 00 5 000 3 3 Rape 10 9 1010 6 10 9 10 9     10 8 9 8 10101010 4  9  8  7 2 7 9 6 9 7 8 10 Rice 7 8 5 7 0 5 -- 3 3 8     8 8 3 3 4 7 3 1  0  4  2 00 3 0 2 0 2 5 Sicklepod 10 6 8 8 6 10 -- 7 7     10 8 8 4 8 8 1010 5  5  6  3 0 5 5 0 4 2 5 8 Soybean 8 6 7 10 7 7 -- 9 7     7 9 10 5 -- 6 10 10 5  6  6      34 4 8 7 7 4 5 4 Sugar beet 10 10 101010101010101010101010 9 10 10 10     10  10  10 0 9 9 10 10 3 10 10 Teaweed 3 7 8 6 7 10 -- 7 8 10 2 4 2 7 3     7 9 2  6  5  3 0 3 2 0 4 2 2 5 Velvetleaf 10 -- 10 -- 4 10 -- 6 7 7 3 4     -- 8 3 8 10 0  5  6  30 5 8 0 3 4 5 7 Wheat 2 1 1 0 0 3 6 4 3 3 6 4 0 4     0 7 4 2  0  2      20000 1 000 Wild buckwheat 9 10 1010 5 10 8 10 9 1010101010 8 1010 9  7      10  3 0 9 9 4 -- -- 5 10 Wild Oat 5 4 10 1 0 9 7 5 5 8 8 10 4 8 3 10 7     3  0  2      30 3 4 0 4 2 2 7     COMPOUND (250 g/ha) 25 28 32 33 34 35 36 37 40 43 44 45 46 48 50 53 55     56 57 61 68 69 71 73 74 75 76 82       POSTEMERGENCE Barley 2 0 0 0 0 0 2 5 0 0 3 0 4 0 1 3 0 0 4 4 2 2 2 5 4 0      3 2 Barnyardgrass 10 0 10 10 2 2 10 4 3 9 5 0 5 9 3 10 7 0 7 9 7 6 10 6     10 6 4 3 Blackgrass 10 2 8 3 3 0 5 1 0 2 7 0 8 6 9 9 8 5 10 7 10 5 10 9     10 3 10 3 Chickweed 9 0 10 3 5 6 1010 9 4 5 0 7 9 10 10 10 4 10 6 10 7     10 10 10 2 10 8 Cocklebur 3 2 7 4 2 5 7 6 6 5 0 0 5 5 5 6 7 0 6 7 -- --     5 2 4 5 9 3 Corn 2 0 1 0 0 0 4 2 2 0 0 0 3 1 3 4 3 0 3 4 2 1 4 6 4 2 2 2     Cotton 2 0 5 -- 0 6 4 8 7 2 4 3 3 8 0 4 1 4 7 9 6 7 10 5 5 2 7 2     Crabgrass 9 2 8 9 5 2 10 10 9 9 7 3 5 10 10 10 10 5 9 10 10 10 10 8 10 9     5 10 Downy brome 2 00000 1 00000 3 0 3 000 6 3 2 1 4 5 3 0 2 2 Giant     foxtail 10 2 10 10 0 0 10 10 4 -- 6 0 10 8 -- -- -- 0 7 9 8 6 9 9 10 6 3     7 Green foxtail 9 2 10 6 3 5 10 9 4 5 5 0 7 7 6 7 9 3 7 10 8 6 9 7 10 3     5 2 Jimsonweed 10 7 10 10 7 10 10 9 9 7 6 6 10 10 8 10 10 8 10 10 10 7     10 9 10 7 7 9 Johnsongrass 3 0 8 4 0 0 10 1 1 -- 3 0 7 5 8 10 -- 0 6 8 6     5 7 6 7 2 4 -- Lambsquarters 10 5 10 7 3 10 10 10 10 10 9 9 10 10 8 10     10 8 10 10 10 10 10 10 10 6 9 9 Morningglory 8 2 7 5 0 5 8 4 2 5 7 0 7 6     -- 7 7 7 10 10 7 7 9 8 8 3 8 5 Nutsedge 5 0 3 3 000000 -- -- 4 0 0 3 2     -- -- 3 6 0 0 5 5 000 Rape 9 2 10 6 6 10 10 10 9 5 6 3 10 8 8 10 8 4 10     8 10 7 10 7 8 5 9 8 Rice 3 1 0000 4 4 1 0 3 0 5 8 3 5 2 0 3 5 3 3 7 6 7     2 2 3 Sicklepod 5 2 10 4 0 4 8 4 -- 2 5 4 10 6 4 8 6 5 8 8 6 7 8 5 4 3 8     7 Soybean 9 2 6 3 5 4 8 7 5 6 6 0 8 6 -- 7 5 6 7 9 9 6 7 9 10 5 5 5     Sugar beet 10 0 10 10 10 10 10 10 10 9 10 10 10 10 10101010101010 9     1010101010 9 Teaweed 5 0 5 4 4 -- -- 5 4 2 6 4 3 6 3 6 4 3 10 10 7 7 8 0     0 0 6 2 Velvetleaf 9 -- 2 1 0 3 5 5 6 3 3 0 8 9 -- 8 -- 2 8 10 4 6 7 0     -- 5 7 3 Wheat 000000 1 00000 1 1 0 0000 3 3 2 2 2 2 0 3 0 Wild buckwheat      9 0 10 10 6 0 10 10 9 10 6 0 9 4 10 10 10 3 10 7 10 9 10 10 10 10 -- 7     Wild Oat 5 0 1 00 2 4 2 0000 4 2 3 5 1 0 6 6 4 3 4 6 3 0 4 2       COMPOUND (250 g/ha) (125 g/ha) 84 87 90 104 107 117 3 8 15 16 17 23 25 2     8 32 33 34 35 36 37 40 43 44 46 48 50 53 55       POSTEMERGENCE Barley 6 4 1 0 3 2 0 2 0 0 0 2 1 0 0 0 0 0 2 1 0 0 0 2 0 0      0 0 Barnyardgrass 10 6 5 1 4 5 0 7 8 0 3 5 8 0 3 3 0 2 9 1 0 0 3 3 9 3     7 7 Blackgrass 9 10 4 0 3 5 0 2 8 02 8 9 0 2 000 3 000 3 3 2 9 7 7     Chickweed 10 9 8 8 9 8 0 3 2 0 2 9 5 0 6 2 0 -- 10 6 7 0 3 3 7 6 9 5     Cocklebur 6 3 2 5 6 0 0 2 00 2 3 2 0 6 3 0 3 7 5 6 4 0 3 5 5 5 5 Corn 5     5 3 0 1 2 0 2 1 0 2 0000000 2 2 2 0 0 2 1 2 2 3 Cotton 9 4 3 6 3 20 1 4     0 3 2 00 5 00 4 4 8 7 1 4 3 8 0 2 1 Crabgrass 10 10 2 0 8 7 0 3 9 2 0 8     8 10 3 3 2 1 8 6 6 6 5 3 2 9 8 9 Downy brome 6 5 00 1 2 00 2 002     00000000000 2 0 2 0 0 Giant foxtail 10 8 2 0 2 5 0 5 7 00 7 9 0 7 6 00     10 3 0 -- 3 9 6 -- -- -- Green foxtail 10 8 2 0 2 2 0 6 9 0 2 8 8 0 -- 5     0 3 9 3 1 00 5 5 4 -- 8 Jimsonweed 10 10 5 9 9 10 0 5 10 00 10 10 2 10 5     3 10 10 8 9 5 5 10 10 8 9 10 Johnsongrass 10 7 00 2 2 0 2 2 00 3 2 0 --     000 2 00 4 3 -- 2 -- -- -- Lambsquarters 10 10 2 10 10 3 0 8 10 2 5 9 9     2 10 6 3 10 10 10 10 6 7 10 10 8 10 10 Morningglory 10 10 3 8 7 1 0 -- 7     2 2 0 8 2 5 5 0 5 2 2 1 -- 3 7 5 8 5 6 Nutsedge 5 2 000 -- 0 2 000 2 3     00 2 000000 -- 00 0 0 0 Rape 10 9 3 8 8 5 0 7 8 0 2 9 9 2 -- 6 2 10 10 8     8 5 4 10 6 7 8 6 Rice 4 2 1 0 4 1 0 2 2 00 2 2 00000 2 3 1 -- 0 4 2 3 3     1 Sicklepod 10 9 5 5 4 3 0 3 3 0 3 2 3 0 9 2 0 4 8 2 8 2 3 9 5 4 6 4     Soybean 7 7 3 5 5 3 3 7 7 4 33 9 0 5 3 2 4 5 7 5 4 4 6 5 -- 6 5 Sugar     beet 10 10 8 10 10 10 0 8 10 0 9 10 9 0 9 10 8 10 10 10 10 8 8 10 10 10     10 10 Teaweed 6 7 0 5 4 2 00 3 00 2 5 0 33 0 4 4 4 -- 0 3 0 6 3 4 4     Velvetleaf 7 9 0 5 5 3 0 3 2 2 5 6 7 -- 000 1 4 5 6 0 3 8 5 -- 7 9 Wheat     5 3 2 0 1 000 1 000000000000000 1 0 0 0 Wild buckwheat 10 9 7 7 10 30 5     -- -- 3 10 9 0 10 9 0 -- 10 10 6 10 4 7 0 -- 10 10 Wild Oat 7 7 00 2 20     1 2 0 1 3 3 00000 2 1 000 3 1 2 2 0       COMPOUND (125 g/ha) (62 g/ha) 56 57 61 68 69 71 73 74 75 76 82 84 87     90 104 107 117 5 8 15 16 17 23 25 32 33 34 35       POSTEMERGENCE Barley 0 0 3 1 2 1 5 0 0 1 0 5 2 1 0 2 2 0 0 0 0 0 0 0 0 0      0  0 Barnyardgrass 0 6 6 6 6 -- 5 6 4 3 2 8 6 00 4 4 0000000000  0     Blackgrass 0 7 6 8 4 10 9 10 2 7 3 8 8 2 0 0 2 00 4 00 5 5 000  0     Chickweed 3 8 6 9 5 9 5 10 0 10 5 10 7 2 5 8 6 2 0 1 00 8 3 6 00  0     Cocklebur 0 5 5 -- -- 5 2 3 4 7 2 6 3 2 4 5 0 2 0000 3 2 4 3 0  0 Corn0     2 3 00 3 5 3 0 -- 0 4 4 2 0 1 0 0 2 00 1 00000  0 Cotton 3 6 6 6 7 3 5 3     1 6 2 5 4 2 6 2 2 0 1 3 0 1 00 4 00  3 Crabgrass 2 7 10 10 10 -- 8 10 4     -- 7 7 6 00 4 6 00 4 00 4 5 3 3 0  0 Downy brome 000 1 1 3 5 1 000 5 4     0000 00000 2 0000  0 Giant foxtail 0 6 7 7 5 5 7 7 00 2 7 5 0 00 2 0 2 2     00 2 8 0 6 0  0 Green foxtail 0 6 7 7 4 9 7 10 2 2 0 5 6 0 0 00 0 2 4 00     5 4 7 00  0 Jimsonweed 6 10 10 10 6 10 9 5 6 7 7 10 10 2 8 9 8 -- 5 9 00     8 9 10 3 0  4 Johnsongrass 0 4 6 5 4 1 6 3 0 3 -- 6 4 000 2 0 1 00000 8     00  0 Lambsquarters 7 10 10 10 10 10 9 10 6 8 9 10 10 0 9 7 2 8 5 8 0 2     8 8 10 5 0  8 Morningglory 7 10 8 7 7 5 8 7 2 7 3 10 9 3 4 5 0 -- -- 7 2     0 -- 8 5 5 0  3 Nutsedge -- -- 0 3 000 1 000 4 0000 -- 000000 2 000  0     Rape 3 10 7 10 7 7 5 8 3 9 3 10 8 3 8 8 3 4 3 7 00 8 9 10 5 0  6 Rice 0     2 4 2 2 4 3 5 0 1 2 3 2 1 0 4 1 0000000000  0 Sicklepod 4 7 7 5 7 7 2 --     3 6 2 10 6 5 4 4 2 4 000 2 2 3 6 -- 0  2 Soybean 5 7 7 7 6 7 8 10 4 5 5     6 6 3 5 4 3 4 7 6 3 2 3 9 5 2 0  4 Sugar beet 7 10 10 10 9 10 8 10 9 10     9 10 10 7 10 10 10 7 6 10 0 8 10 9 4 10 5 10 Teaweed 3 9 8 7 6 7 000 5 0     5 6 0 4 4 1 3 00000 2 3 3 0  4 Velvetleaf 0 7 10 3 6 4 0 -- 5 -- 0 6 8     00 -- 2 3 3 0 0 3 4 5 000  0 Wheat 000 2 1 000000 4 2 1 0 1 0 0000000000      0 Wild buckwheat 0 9 7 10 9 9 9 10 -- -- 3 10 9 5 5 6 0 5 3 -- -- 0 8 5     5 3 0  0 Wild Oat 0 3 5 3 2 3 5 3 0 2 0 5 5 00 2 0 00 1 00 2 0000     0       COMPOUND (62 g/ha) (31 g/ha) 36 37 40 46 48 50 53 55 56 57 61 68 6     9 71 73 74 76 82 84 87 90 104 107 117 8 17 23 25       POSTEMERGENCE Barley 0 0 0 2 0 0 0 0 0 00 1 1 0 0 0 1 0 3 0 0 0 2 0 0     0  0  0 Barnyardgrass 9 000 5 0 5 5 0 5 3 3 5 4 2 0 -- 2 6 5 0000 0 0  2      2 Blackgrass 00000 4 7 1 0 5 4 5 2 7 5 8 4 2 7 8 000 2 00  3  2     Chickweed 9 3 3 0 5 5 6 3 0 7 5 6 5 6 4 4 8 2 10 7 0 4 4 3 00  5  0     Cocklebur 7 4 6 3 -- 4 -- 5 0 4 3 -- -- 5 2 3 6 2 5 2 0 3 4 0 00  2  0     Corn 0 1 2 0 1 2 1 3 00 2 00000 1 0 3 3 00 1 0 00  0  0 Cotton -- 8 7 2     7 0 2 0 3 5 3 5 6 3 4 0 -- 0 4 2 2 6 1 0 1 1  0  0 Crabgrass 1 4 4 2 --     7 8 7 0 6 10 10 10 10 3 2 5 2 6 5 00 4 6 00  2  2 Downy brome 000000     000001 1 2 00004 3 0000 00  0  0 Giant foxtail 3 00 3 4 -- -- -- 0 5 6 6     4 3 4 5 00 5 3 000 2 00  0  0 Green foxtail 4 1 0 3 3 3 6 1 0 4 5 5 3 6     6 9 -- 0 3 4 0000 00  2  3 Jimsonweed 9 7 8 5 9 6 9 6 5 10 10 6 6 10 7 4     7 7 10 9 0 8 7 6 3 0  8  8 Johnsongrass -- 00 -- 0 8 8 5 0 3 33 3 0 2 0     -- 2 3 3 0000 00  0  0 Lambsquarters 10 9 10 9 9 7 10 8 6 10 9 10 9 9 5     7 6 9 10 9 0 9 5 2 5 0  7  5 Morningglory 0 -- 1 5 -- 6 5 5 6 10 6 7 7 5     5 6 7 0 10 9 3 -- 5 0 -- 0  0  7 Nutsedge 0 -- 0000 00 -- -- 00000000 3     0000 -- 00  0  0 Rape 10 8 8 5 -- 7 5 5 3 8 6 8 7 4 2 2 6 3 4 7 0 4 6 2     0 0  7  8 Rice 0 3 1 2 1 0 3 -- 0 2 3 00 2 2 0 1 0 2 0 1 0 3 0 00  0  0     Sicklepod 5 1 -- 8 5 3 3 4 3 6 7 4 6 6 0 4 5 0 7 5 4 4 3 2 00  0  0     Soybean 4 6 5 4 4 6 4 4 4 6 6 6 5 3 5 10 5 3 4 5 3 4 4 3 6 0  3  9 Sugar     beet 10 10 10 10 10 9 10 10 6 10 9 8 7 10 3 10 10 5 10 10 7 10 9 8 6 7     10  8 Teaweed 3 3 4 0 5 0 3 3 0 9 8 6 4 5 00 2 0 4 5 0 4 2 1 00  0  0     Velvetleaf 0 4 6 3 4 -- 6 8 0 7 6 3 6 -- 0 -- 7 0 5 8 00 3 1 3 0  0  2     Wheat 000000 000001 000000 3 000 1 0 0 0  0  0 Wild buckwheat 8 9 3 7 0     10 -- 10 0 8 6 7 7 6 7 8 -- 0 8 9 0 4 5 0 00  7  5 Wild Oat 000 2 1 0     0000 3 1 1 2 4 0 2 0 4 3 00 1 0 00  0      0                                   COMPOUND (31 g/ha) (1000 g/ha) (500     g/ha) 32 33 34 35 36 37 40 50 53 55 57 68 69 76 84 117 3 5 9 13 28 43 75 1     04 3 5  8      9     POSTEMERGENCE PREEMERGENCE Barley 0 0 00  0 0 0 0 0 0 0 1 1 0 0 0 0 3 0     5 2 0 0 2 0 3  2  0 Barnyardgrass 0000 9 000 2 3 3 0 3 0 3 0 10 10 3 10     10 10 9 8 2 10 10  0 Blackgrass 0000000 2 4 1 3 4 0 4 6 2 5 10 5 10 8 10     8 7 3 10 10  3 Chickweed 3 000 8 00 4 3 1 5 0 3 7 8 0 9 10 9 10 5 9 9 6     2 9 10  7 Cocklebur 1 1 00 4 3 6 4 5 4 3 -- -- 4 00 3 8 3 4 2 5 7 3 0 7     3  0 Corn 00000 1 1 1 1 0000 1 00 2 8 0 4 8 3 3 4 0 2 10  0 Cotton 2 00     -- -- 8 7 0 1 0 4 4 6 5 3 0 5 4 00000 2 3 --  0  0 Crabgrass 0000 1 4 --     3 2 1 3 10 5 000 10 10 10 10 10 10 10 10 10 10 10 10 Downy brome     00000000000 1 1 0 3 0 4 3 0 10 2 0 4 2 3 2  3  0 Giant foxtail 0000000     -- -- -- 3 6 3 0 2 0 10 10 10 10 10 10 10 10 1 10 10 10 Green foxtail     0000 3 1 0 1 1 0 3 3 0000 10 10 10 10 10 10 10 10 10 10 10  8 Jimsonweed     9 00 -- 9 7 8 -- 6 6 10 6 5 6 6 5 9 10 8 10 10 10 6 7 8 10 10  5     Johnsongrass 0000000 5 00000000 8 10 0 10 10 8 7 7 6 5 10      0 Lambsquarters 8 3 0 3 10 9 9 4 4 4 10 10 7 4 9 0 10 10 10 10 10 10 9     10 9 10 10 10 Morningglory 0000 -- -- -- 6 3 3 10 6 7 5 4 0 9 10 7 10 10     9 5 4 3 9 10  3 Nutsedge0000000000 -- 0000 -- 5 4 3 5 5 0 3 7 0 --  5  2     Rape 9 3 0 5 10 6 4 2 5 3 4 7 7 4 3 0 10 10 9 10 10 10 7 5 5 10 10  6     Rice 000000 1 000 2 00 1 00 3 5 0 10 4 0 4 0 0 2  0  0 Sicklepod 4 -- 00     5 1 4 3 3 -- 6 3 5 44 1 6 10 7 10 9 0 7 9 0 10  9  3 Soybean 2 2 0 3 3 5     4 4 4 3 3 6 5 5 0 2 4 7 3 4 6 4 0 4 0 4  8  2 Sugar beet 0 9 5 10 10 10     9 8 10 5 10 6 7 10 10 2 8 10 10 10 10 9 6 9 5 10 10  6 Teaweed 2 0003 3     4 000 8 5 3 0 3 0 9 10 8 10 3 5 7 7 8 10 10  5 Velvetleaf 00000 -- 4 0 6     5 5 3 6 3 3 1 5 10 9 10 10 10 6 8 0 10 10  5 Wheat 0000000000000000 0 1     000000 0 0  0  0 Wild buckwheat 4 3 0 0 5 2 0 4 10 7 3 7 6 -- 4 0 9 10 9     10 9 6 7 7 9 9 10  8 Wild Oat 00000000000 1 1 0 2 0 2 9 0 7 5 3 5 5 0 8     8      0                                                                       C     OMPOUND (500 g/ha) 13 15 16 17 23 25 28 33 34 35 36 37 40 43 44 45 46 48 5     0 53 55 56 57 61 68 69 71 73       PREEMERGENCE Barley 3 3 0 3 3 00 00 1 7 7 4 0 5 0 2 2 0 5  4 4 5 --3 1 5      5 Barnyardgrass 10 10 10 10 10 10 101010101010101010101010 1010101010     -- 10101010 Blackgrass 8 10 9 101010 6 10 6 7 1010101010 8 1010 --     10101010 -- 8 101010 Chickweed 7 10 2 101010 2 8 8 5 10 5 8 8 10 8 10 8     8 1010 7 8 -- 9 101010 Cocklebur0 0 0 4 2 0 0 -- 5 5 10 2 0 3 0 0 3 0     1010 7 8 10 -- 6 0 3 3 Corn 3 5 3 7 8 3 6 3 2 4 8 3 3 0 10 2 5 6 3 7 6 7     8 -- 4 2 7 9 Cotton 0 0 2 0 2 5 0 0 0 2 3 0 7 0 0 0 1 1 2 3 3 0 8 -- 4 9     8 2 Crabgrass 10 10 10 10 10 10 101010101010101010101010 1010101010101010     1010 Downy brome 3 4 0 3 7 -- 0 0 0 1 5 4 4 0 3 0 5 4 4 10 6 5 10 -- 4 5     10 6 Giant foxtail10 10 10 10 10 10 101010101010101010 81010 1010101010     -- 10101010 Green foxtail 10 10 10 10 10 10 101010101010101010101010     1010101010 -- 10101010 Jimsonweed 10 10 3 101010 8 6 10101010 9 9 10 0 7     10 9 1010 2 101010101010 Johnsongrass 8 10 9 9 10 10 10 1010101010 9 7     101010 8 9 10 9 1010 -- 4 4 9 10 Lambsquarters 1010 9 1010101010101010101     01010101010 10101010101010101010 Morningglory 10 9 3 6 10101010 7 9     101010 8 10 7 7 8 9 10 9 1010 -- 10 9 4 9 Nutsedge 2 5 0 6 10 0 2 3 0 0     7 10 6 0 -- -- 3 0 3 5 3 -- -- 9 3 10 4 6 Rape 1010 5 101010 6 10 6     10101010 9 10101010 -- 10101010 -- 10101010 Rice 3 3 3 2 8 2 2 0 5 1 5 2     0 0 9 1 2 6 0 3 3 3 8 8 2 3 3 4 Sicklepod 7 4 0 7 8 8 9 9 3 8 10 5 8 0 3     2 3 4 3 10 9 0 3 101010 9 -- Soybean 3 4 0 4 5 3 4 10 3 1 7 3 4 3 9 0 4     5 2 6 4 10 6 -- 6 4 7 9 Sugar beet101010101010 2 9 1010101010 7 1010 9     10 -- 10101010 -- 10101010 Teaweed 5 8 0 7 10 8 2 3 10 3 1010 8 4 8 0 8     10 9 10 9 2 8 1010 9 9 3 Velvetleaf 1010 8 101010 9 9 1010101010 9 10 8     10 10 10101010101010 9 10 7 Wheat 0 2 0 0 2 0 0 0 0 0 3 0 0 0 2 0 1 1 0     3 3 0 1 -- 0 2 4 0 Wild buckwheat 9 10 0 8 9 10 5 10 4 0 10 9 8 5 9 8 10     9 3 10 5 1010 -- 10 10 9 9 Wild Oat 3 9 0 5 10 4 3 1 1 0 -- 7 7 3 3 2 7     8 6 10 10 4 10 -- 5 7 9 10       COMPOUND (500 g/ha) (250 g/ha) 74 75  76 82 84 87 90 104 107 117 5 8 9 1     3 15 16 17 23 25 28 32 33 34 35 36 37 40       PREEMERGENCE Barley 6 0 4 4 5 2 7 2 3 0 0 0 0 0 2 0 0 2 0 0 0 0 0 0 3     3 2 Barnyardgrass 10 8 8 10 10 10 8 6 10 10 6 10 0 5 10 8 8 10 10 10     1010 1010 1010 10 Blackgrass 10 8 8 10 10 10 9 6 10 10 5 9 0 3 9 4 8 10     10 5 10 8 5 3 10 10 9 Chickweed 10 8 9 10 10 10 10 4 7 9 8 10 5 3 7 0 10     8 10 0 7 8 6 5 10 3 6 Cocklebur 10 000 5 5 2 3 0 4 4 3 0 0 0 0 4 0 0 0 0     9 0 -- 0 -- 0 Corn 5 2 3 5 6 4 7 2 2 4 2 5 0 2 3 1 4 7 2 5 2 1 2 3 7 2 2     Cotton3 0 4 1 4 2 0000 2 000000 1 00000 2 2 00 Crabgrass 10 10 10     10101010101010 10 10 8 10 10101010101010101010101010 Downy brome 4 3 5 6     10 5 3 2 0 3 1 0 00 2 00 3 1 00000 1 2 2 Giant foxtail 10 10 10 10 10 10     9 10 10 10 7 10 7 10 10101010101010101010101010 Green foxtail10 10 10 10     10 10 9 10 10 10 5 10 3 10 10101010101010101010101010 Jimsonweed 9 3 6 9     10 10 10 5 6 10 5 10 3 5 10 0 10 10 10 2 5 5 9 5 10 9 8 Johnsongrass 8 6     7 10 10 10 7 6 0 9 2 10 0 3 10 2 7 10 10 101010101010 9 8 Lambsquarters     9 9 9 10 10 10 10 9 9 10 9 10101010 9 101010 8 10101010101010 Morningglor     y 10 3 7 9 10 10 8 4 6 9 5 10 0 0 9 0 3 10 7 5 7 47 8 9 9 10 Nutsedge 5     3 3 3 3 5 2 3 6 8 0 3 0 0 2 0 2 8 0 0 0 3 0 0 5 6 4 Rape 10 6 10 5 10 10     10 5 6 10 8 10 4 8 10 3 9 1010 4 10 0 3 10101010 Rice0 3 0 2 6 7 3 00 5     1 0 0 0 2 0 0 7 10 0 1 0 5 1 1 0 0 Sicklepod 10 7 9 7 10 10 3 6 3 4 9 9     0 3 2 0 3 8 0 0 0 -- -- 3 10 0 5 Soybean 9 0 4 1 9 7 4 3 3 4 2 5 0 2 3 0     2 4 0 2 30 2 0 4 0 3 Sugar beet 10 3 10 10 10 10 8 7 6 10 8 10 3 5 10 2     101010 0 9 9 10 -- 101010 Teaweed 7 5 7 9 10 10 6 5 5 10 8 7 3 0 8 0 5 5     7 0 4 3 4 3 3 9 8 Velvetleaf 8 4 7 8 10 10 10 7 6 10 8 10 3 4 10 8 1010     8 8 10 8 1010101010 Wheat 3 0 4 1 2 00000 0 0000000000000 2 00 Wild     buckwheat 4 3 5 10 9 9 8 4 8 10 9 9 5 6 10 0 8 7 10 2 4 3 00 9 7 5 Wild     Oat 5 4 7 9 10 6 4 4 4 0 5 2 0 0 4 0 2 10 3 00000 3 5 3       COMPOUND (250 g/ha) (125 g/ha) 43 44 45 46 48 50 53 55 56 57 61 68 69     71 73 74 75 76 82 84 87 90 104 107 117 8 13       PREEMERGENCE Barley 0 2 0 0 2 0 4 3 0 4 1 3 0 4 4  0 0 3 3 2 2 3 0 2 0 0      0 Barnyardgrass 8 10 8 9 10 10 10 10 8 10 10 10 10 10 10 10 6 7 9 10 10     6 4 8 6 10 5 Blackgrass 7 10 4 10 10 10 10 10 10 10 10 4 -- 101010 7 8     10 9 9 7 6 7 10 7 3 Chickweed 5 8 3 10 4 7 10 8 7 4 4 9 7 9 1010 7 8     101010 7 3 5 8 10 3 Cocklebur 000 2 0 10 7 -- -- 1 4 5 -- 0 -- 6 0 0 0 3     4 0 0 0 3 00 Corn 0 6 1 1 3 3 6 5 6 6 3 3 1 5 8 3 0 2 5 6 4 3 0 0 0 2 2     Cotton 0 00 1 1 0 2 0 0 3 3 4 6 3 0 2 0 4 0 1 0 0 0 0 000 Crabgrass 10     10 10 10 10 1010101010101010101010101010101010 7 101010 10 Downy brome     000 3 3 3 10 3 0 10 3 3 4 6 3 3 0 4 3 4 3 0 2 0 0 00 Giant foxtail 10 10     7 10 10 101010101010 7 5 10101010101010 8 9 9 1010 10 10 Green foxtail10     10 10 10 10 10101010101010101010101010101010 9 101010 10 10 Jimsonweed 6     8 0 5 8 7 10 7 0 101010 7 1010 8 0 6 9 1010 4 3 5 69 5 Johnsongrass 6 10     8 9 8 9 9 8 101010 4 4 9 10 7 3 6 9 8 8 3 3 0 6 7 3 Lambsquarters 10 10     10 8 10 1010101010101010 9 10 9 7 7 10101010 8 9 10 10 10 Morningglory 7     8 7 5 0 8 10 8 1010 9 9 7 3 9 7 3 7 5 1010 8 4 3 8 7 0 Nutsedge 0 -- --     2 0 3 3 0 -- -- 8 0 2 3 5 3 3 3 2 0 5 0 0 3 000 Rape 6 8 0 8 810101010101     010 9 8 1010 5 10 5 1010 7 4 4 510 8 Rice 0 8 0 1 50 3 2 0 7 7 2 3 2 3 0     3 0 2 6 6 2 0 0 3 00 Sicklepod 00 2 2 2 2 9 6 0 2 8 1010 8 3 9 3 8 5     1010 3 3 3 05 3 Soybean 0 5 0 2 3 2 5 3 9 5 3 5 2 7 8 6 0 3 1 7 6 3 2 3     25 2 Sugar beet 5 10 6 9 10 9 10 9 10101010 8 8 1010 2 10101010 8 6 4 90     10 5 Teaweed 3 7 0 4 8 8 10 8 0 7 1010 9 9 2 6 3 6 8 10 9 2 4 3 4 5 0     Velvetleaf 8 9 7 8 10 10101010101010 9 10 7 7 0 5 8 101010 6 3 10 10 4     Wheat 0000 1 0 0000000 2 0 2 0 2 0000000 00 Wild buckwheat 4 5 4 10 9 2     10 4 10 10 9 10 -- 9 -- 2 0 3 9 9 8 8 3 7 6 9 6 Wild Oat 2 00 5 6 5 10 7     4 10 8 5 4 7 9 3 0 6 7 9 3 2 4 3 000       COMPOUND (125 g/ha) 15 16 17 23 25 28 32 33 34 35 36 37 40 43 44 45 46 4     8 50 53 55 56 57 61 68 69 71 73       PREEMERGENCE Barley 10 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 2 0 3 2 0 1 0 3 0      3 3 Barnyardgrass 9 2 5 10 4 8 1010 9 6 1010 8 6 10 4 7 10 10 10 10 4     10 10 9 10 10 8 Blackgrass 9 2 5 9 10 2 10 8 1 2 8 10 4 6 -- 0 9 9 8 10     8 7 3 5 2 5 10 9 Chickweed 6 0 10 5 8 0 5 8 0 5 9 2 3 3 4 0 9 3 5 9 7 2     2 -- 7 6 5 10 Cocklebur 0 0 3 0 0 0 0 5 0 0 0 0 -- -- -- 0 0 0 10 6 5     000 4 -- 0 -- Corn 2 0 0 4 0 2 0 0 0 2 5 0 0 0 4 0 0 1 3 6 4 5 5 2 2 0 3     6 Cotton 0 0000000 10 00000000 1 0 2 00 -- 3 0 5 2 0 Crabgrass 10 9     101010101010 0 9 1010101010101010 10 10 10 10 10 10 10 -- 10 10 Downy     brome 0 0 0 2 0 0 0 0 10 0 00000000 3 5 2 0 5 2 00 4 0 Giant foxtail 10     9 10101010101010101010101010 7 1010 10 10 10 10 10 10 -- 3 10 10 Green     foxtail 10 9 101010101010 8 101010101010101010 10 10 10 10 10 10 10 10     10 10 Jimsonweed 9 0 7 10 7 2 5 3 8 2 9 6 5 3 0 0 2 4 6 10 6 0 8 8 9 7 8     9 Johnsongrass 9 0 3 1010 6 9 1010 9 10 8 7 5 10 8 7 5 8 9 7 8 8 7 2 0 9     8 Lambsquarters 9 8 10 9 10 5 1010 2 9 101010101010 8 8 10 10 10 10 10     10 10 10 9 10 Morningglory 5 0 2 9 3 4 4 2 0 7 8 8 8 4 4 0 2 0 7 10 7 7     9 88 3 3 5 Nutsedge 0 0 0 3 0 0 0 0 2 0 5 3 2 0 -- -- 0 0 3 3 0 -- -- 4     0 2 1 3 Rape 7 0 3 1010 0 5 0 0 4 101010 0 0 0 8 810 10 7 10 10 10 10 4     8 10 Rice 0 0 0 4 00 1 000 1 000 3 0 1 2 0 3 0 0 4 2 0 3 2 2 Sicklepod     000 2 000 5 0 3 5 0 3 00000 2 7 3 0 0 3 5 10 7 0 Soybean 000 2 00 1 0 3     0 3 0000000 2 4 2 2 3 2 4 0 3 6 Sugar beet 10 0 10 10 10 0 8 8 0 9 10 10     10 3 4 2 6 9 8 10 9 10 10 10 6 8 5 10 Teaweed 3 0 2 2 3 0 2 3 0 3 3 9 8     3 00 2 7 5 9 5 0 6 6 9 8 7 0 Velvetleaf 9 3 9 9 5 5 10 -- 0 2 10 8 10 6     9 6 4 9 10 10 10 4 10 10 7 9 10 3 Wheat 000000000000000000 0 000000000     Wild buckwheat 10 0 7 7 8 0 3 000 8 5 2 3 5 3 9 8 0 10 3 6 3 8 -- -- 9 9     Wild Oat 3 00 10 000000 2 00000 3 3 3 10 5 0 6 6 4 4 6 4       COMPOUND (125 g/ha) (62 g/ha) 74 75 76 82 84 87 90 104 107 117 5 8 15     16 17 23 25 32 33 34 35 36 37 40 44 45 46 48 50       PREEMERGENCE Barley 0 0 2 3 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0  0      0  0  0  0 Barnyardgrass 7 3 5 3 10 10 4 3 3 3 5 9 8 0 2 9 3 10 5 7 2 9     6 6  6  2  5  6 10 Blackgrass 9 6 7 9 5 7 4 3 6 7 3 4 3 0 3 7 8 3 000 3     5 2  9  0  9  0  8 Chickweed 9 3 7 8 9 8 7 3 0 5 8 10 4 0 6 3 5 4 00 5 4     00 --  0  7  0  3 Cocklebur 3 0000 3 0000 0000 3 0 -- 0000 -- 0 -- -- --       0  0  3 Corn 000 1 5 00000 1 0000 2 0000 1 3 00  4  0  0  0  3 Cotton     00 4 0000000 -- 0000000000000  0  0  0  0  0 Crabgrass 10 10 10 10 10 10     10 7 8 10 9 10 10 8 9 10 10 10 10 10 7 10 10 10 1010101010 Downy brome 2     0 3 2 2 00000 00000000000000  0  0  0  0  0 Giant foxtail 10 7 10 10 10     7 7 8 10 10 6 9 10 6 9 10 10 10 10 8 10 10 10 10  5  2  9  8 10 Green     foxtail 10 10 9 10 10 10 9 7 10 10 3 10 10 8 7 10 10 10 10 10 10 10 10     10  6  3 10 10 10 Jimsonweed 7 0 4 3 10 10 2 3 3 4 3 5 2 0 3 4 1 2 00 2     7 2 4  0  0  2  3  5 Johnsongrass 6 0 5 3 7 7 0000 0 3 8 00 8 5 9 0 7 7     8 5 6  8 --  7  0  7 Lambsquarters 9 4 5 9 10 10 10 7 6 10 9 10 9 8 9 9     10 9 7 9 9 10 8 10 10  6  8  3  9 Morningglory 6 0 4 2 10 10 2 0 3 6 3 2     2 00 5 2 3 1 00 2 5 3  0  0  2  0  5 Nutsedge 3 3 000 4 0000 -- 0000 --     00000 3 3 0 -- --  0  0  3 Rape 8 3 9 5 10 10 2 3 3 0 4 8 2 00 6 3 4 000     9 8 5 --  0  3  3  4 Rice 0 3 00 5 5 0000 00000 4 00000 1 00  2  0  0  0      0 Sicklepod 8 3 7 2 3 10 2 2 00-- 3 00000000 -- -- 0 3  0  0  0  0  0     Soybean 4 0 2 1 3 5 0 2 3 0 1 2 000000000000  0  0  0  0  0 Sugar beet     10 0 7 9 10 10 8 5 33 7 9 7 0 10 10 5 5 3 0 8 7 5 5  4  0  6  3  6     Teaweed 5 3 5 5 5 7 0 4 0 3 7 3 0000 2 000 2 2 3 5  0  0  2  2  4     Velvetleaf 4 0 4 7 10 10 9 6 0 8 4 10 5 0 8 8 0 10 0 -- 2 9 6 5  0  0  2      9  7 Wheat 0000000000 00000000000000  0  0  0  0  0 Wild buckwheat 00 2     9 9 7 7 0 6 5 7 5 3 0 3 5 5 0000 3 2 0  4  0  7 --  0 Wild Oat 3 0 5 4 3     00 3 00 4 0 2 00 3 00000 1 00  0  0  2  0      0                                COMPOUND (62 g/ha) (31 g/ha) 53 55 56     57 61 68 69 71 73 74 75 76 82 84 87 90 104 107 117 8 17 23 25 32 33 34     35  PREEMERGENCE Barley 2 0 0 0 0 3 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     0 0 0 Barnyardgrass 7 9 4 10 9 5 8 10 8 5 0 2 2 7 5 3 2 00 3 0 4 0 8 000     Blackgrass 7 8 5 0 3 0 5 10 8 8 4 4 9 5 6 00 5 3 00 3 4 1 000 Chickweed     7 5 0 10 4 5 3 5 4 9 0 7 3 9 7 2 00 3 5 2 3 0000 5 Cocklebur -- 2 00 --     0 -- 00 3 0000 2 0000 00000 -- -- 0 Corn 5 0 3 4 2 000 4 0000 3 00000     00000000 Cotton 0000 3 0 2 1 000 2 0000000 00000000 Crabgrass 10 10 10     1010 1010 1010 1010 1010 10 10 9 7 5 6 9 8 9 10 10 8 10 3 Downy brome 3     0 0 3 000000000000000 00000000 Giant foxtail 10 10 10 10 9 7 3 10 10 9 6     5 8 7 6 2 3 10 10 7 7 10 10 10 9 3 7 Green foxtail 10 10 10 1010 1010     1010 10 7 9 10 10 9 5 4 9 8 10 7 12 10 10 10 10 10 Jimsonweed 8 5 0 2 8     8 6 5 7 5 0 3 2 5 6 0 1 00 2 0 2 0 -- 0 0 0 Johnsongrass 6 6 0 8 7 0 0 3     2 6 00 3 6 5 0000 0 0 4 0 8 0 0 0 Lambsquarters 10 10 9 10 10 10 10 8 9     9 4 5 7 10 10 10 4 3 7 10 8 8 8 7 0 7 0 Morningglory 9 -- 3 4 5 3 2 2 3     5 0 3 0 5 6 00 3 0 0 0 2 0 0 0 0 0 Nutsedge 2 0 -- -- 4 000000000 4 0000     00200000 Rape 8 6 8 0 7 5 2 7 5 6 0 6 3 9 6 0000 80200000 Rice 000 2 2     00000 3 00 3 3 0000 00200000 Sicklepod 5 3 00 2 4 8 00 8 3 5 0 3 7 -- 2     00 3 0 0 0 -- 0 -- -- Soybean 3 0 10 2 2 00 1 000000 3 0 1 3 0 00000000     Sugar beet 10 8 4 10 10 0 7 2 5 10 0 6 8 10 10 8 3 00 9 3 5 4 5 3 5 7     Teaweed8 3 0 6 6 9 8 3 0 3 3 3 3 3 3 0 3 00 0000 -- --02 Velvetleaf 10     10 3 10 8 6 7 8 0 3 0 3 3 8 88 3 0 3 3 3 5 0 10 0 0 0 Wheat 0 00000000000     0000000 00000000 Wild buckwheat 3 0 3 0 7 -- -- 8 -- 000 8 8 5 4 0 3 3 3     0 2 2 0 0 0 0 Wild Oat 5 3 0 6 6 0 3 33 2 00 2 3 00000 00000000       COMPOUND (31 g/ha) 36 37 40 44 45 46 48 50 53 55 56 57 61 68 69 71 73     74 76 82 84 117       PREEMERGENCE Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0     Barnyardgrass 9 4 2 000 2 7 6 8 0 3 7 0 3 3 3 3 00 6 0 Blackgrass 1 3 0     5 0 4 0 7 6 7 00 3 0 3 8 2 7 0 3 2 3 Chickweed 000 3 0 4 00 6 3 0 1 -- 5     2 0 2 8 7 0 33 Cocklebur 00 -- 0 -- 00 -- -- 0 -- -- -- -- 00000000 Corn     000 2 0000 4 00 3 1 000000000 Cotton 000000000000 3 000000000 Crabgrass     8 8 8 10 9 10 9 10 10 10 8 10 10 10 10 10 9 10 9 9 1 6 Downy brome     000000000000 0 000000000 Giant foxtail 10 10 8 0 08 7 10 10 10 3 5 6 3 1     10 5 6 5 7 4 10 Green foxtail 10 10 10 5 0 10 9 10 10 10 9 10 10 7 10 10     8 10 9 9 8 8 Jimsonweed 5 00000 1 4 7 4 0 2 4 5 0 2 5 3 3 0 2 0 Johnsongr     ass 7 4 5 00 3 0 5 5 5 00 5 00 2 0 4 0 2 2 0 Lambsquarters 9 7 9 9 6 5 2     9 10 10 7 6 9 10 0 7 -- 9 5 2 10 7 Morningglory 0 2 3 00 1 0 4 4 2 2 0 5     0 1 1 0 3 2 0 3 0 Nutsedge 000 -- -- 00 3 00 -- -- 0000000000 Rape 9 5 3     000 3 0 4 6 3 0 7 00 0 2 3 4 0 3 0 Rice 00000000000 10 2 000000000     Sicklepod 00 3 00000 3 0000 3 4 00 7 3 000 Soybean 00000000 2 0 1 0 2     000000000 Sugar beet 4 2 2 -- 0 3 0 3 10 4 0 10 10 0 6 00 7 6 0 2 0     Teaweed 1 0 4 0000 3 6 3 0 2 3 -- 000 3 3 000 Velvetleaf 4 3 5 0 -- 1 2     6 9 7 0 7 7 5 4 4 0 00 2 5 3 Wheat 00000000 0 0 0 0 0 000000000 Wild     buckwheat 0 0 0 0 0 4 -- 000 2 0 3 -- -- -- 8 00 2 3 3 Wild Oat1 0000 1     00 3 3 00 5 0 2 2 000000

TEST C

Plastic pots were partially filled with silt loam soil. The soil wasthen saturated with water. Japonica and Indica rice (Oryza sativa)seedlings at the 2.0 to 2.5 leaf stage, seeds selected frombarnyardgrass (Echinochloa crus-galli), bulrush (Scirpus mucronatus),duck salad (Heteranthera limosa), and umbrella sedge (Cyperusdifformis), and sprouted tubers of arrowhead (Sagittaria spp.) and/orwaterchestnut (Eleocharis spp.) were planted into this soil. Severaldays after planting, water levels were raised to 3 cm above the soilsurface and maintained at this level throughout the test. Chemicaltreatments were formulated in a non-phytotoxic solvent and applieddirectly to the paddy water. Treated plants and controls were maintainedin a greenhouse for approximately 21 days, after which all species werecompared to controls and visually evaluated. Plant response ratings,summarized in Table C, are based on a scale of 0 to 10 where 0 is noeffect and 10 is complete control.

    TABLE C       COMPOUND Rate 5 13 15 23 25 28 32 33 34 35 36 37 40 43 44 46 48 50 53     55 56 60 69 71 74 76 82 103       Arrowhead 1000 -- 6 -- -- -- -- -- -- -- -- -- 9 0 6 -- -- -- -- -- -- 8      9 6 7 9 -- -- 0  500 0 4 6 -- -- -- -- -- -- -- 8 8 0 5 7 9 4 7 6 9 7 7     6 6 8 3 4 0  250 0 0 4 -- -- -- 7 4 -- -- 6 -- 0 0 4 6 0 7 6 9 8 7 5 4 6     3 5 0  125 0 0 0 -- -- -- 4 0 -- -- 4 5 0 0 0 6 4 5 4 8 5 7 3 4 6 2 4 0     64 -- 0 0 -- -- -- 3 0 -- -- 0 5 0 0 0 0 0 3 3 8 0 6 0 0 4 0 3 0  32 --     -- 0 -- -- -- 0 0 -- -- 0 -- -- -- 0 0 0 0 0 5 -- -- -- -- -- 0 0 --  16     -- -- -- -- -- -- 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- Barnyardgrass 1000 -- 10 -- -- -- 9 -- -- 10 -- -- 10 10 10 --     -- -- -- -- -- 10 10 10 10 10 -- -- 10  500 8 8 10 10 10 8 -- -- 9 10 10     10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10  250 5 6 10 9 7 6 10     10 9 9 10 10 10 9 10 10 10 10 10 10 9 9 10 10 10 10 10 10  125 0 0 8 9 7     3 10 8 5 8 10 9 8 7 9 10 10 10 10 10 6 9 10 10 10 9 10 6  64 -- 0 5 6 4     0 10 7 0 5 10 8 6 6 6 9 10 10 10 10 4 6 9 10 9 9 8 4  32 -- -- 3 4 0 --     8 4 -- 4 7 -- -- -- 4 6 8 8 9 10 -- -- -- -- -- 8 6 --  16 -- -- -- --     -- -- 6 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     Bulrush 1000 -- 9 -- -- -- 9 -- -- 9 -- -- 9 9 9 -- -- -- -- -- -- 10 9     9 10 9 -- -- 7  500 7 9 10 10 10 9 -- -- 9 9 10 9 9 9 9 9 9 10 10 9 9 9     9 10 9 10 8 7  250 7 9 9 9 9 9 10 9 9 9 9 8 8 9 9 9 9 9 10 9 9 9 9 10 9     9 6 5  125 0 8 8 9 9 0 9 6 4 9 9 7 8 9 7 8 8 9 9 9 4 9 9 10 9 8 5 4  64     --  5 7 9 9 0 6 5 0 6 9 5 0 0 6 8 5 9 7 9 0 7 8 9 8 6 5 3  32 -- -- 0 6     0 -- 5 0 -- 0 6 -- -- -- 0 6 4 9 7 9 -- -- -- -- -- 0 4 --  16 -- -- --     -- -- -- 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     Duck Salad 1000 -- -- -- -- -- -- -- -- 10 -- -- 10 -- -- -- -- -- -- --     -- -- -- 10 10 10 -- -- 10  500 -- -- -- -- -- -- -- -- 10 10 -- 10 --     -- 2 -- 10 -- -- -- -- -- 10 10 10 10 10 10  250 -- -- -- -- -- -- -- --     9 7 -- 10 -- -- 0 -- 0 -- -- -- -- -- 10 10 10 10 10 10  125 -- -- -- --     -- -- -- -- 0 6 -- 10 -- -- -- -- 0 -- -- -- -- -- 10 10 10 10 10 10  64     -- -- -- -- -- -- -- -- 0 0 -- 10 -- -- -- -- 0 -- -- -- -- -- 10 5 10     10 10 10  32 -- -- -- -- -- -- -- -- -- 0 -- -- -- -- --  -- 0 -- -- --     -- -- -- -- -- 9 0 --  16 -- -- -- -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- -- -- -- -- -- -- -- -- -- -- Rice (Indica) 1000 -- 2 -- -- --0     -- -- 4 -- -- 4 3 4 -- -- -- -- -- -- 0 4 5 5 6 -- -- 3  500 0 1 2 4 3 0     -- -- 3 4 3 2 0 2 2 3 3 5 5 7 0 3 3 4 3 0 2 2  250 0 0 0 2 0 0 3 0 2 2 4     1 0 3 0 2 5 4 4 6 0 2 4 4 2 0 0 2  125 0 0 0 0 0 0 2 0 0 2 4 0 0 0 0 0 0     3 2 5 0 0 2 2 0 0 0 0  64 -- 0 0 0 0 0 0 0 0 2 3 0 0 0 0 0 0 0 0 4 0 0 0     0 0 0 0 0  32 -- -- 0 0 0 -- 0 0 -- 0 0 -- -- -- 0 0 0 0 2 3 -- -- -- --     -- 0 0 --  16 -- -- -- -- -- -- 0 0 -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- -- -- -- -- -- Rice (Japonica) 1000 -- 0 -- -- -- 3 -- -- 6 --     -- 5 4 4 -- -- -- -- -- -- 0 5 6 5 8 -- -- 3  500 0 0 1 5 4 0 -- -- 4 5     4 3 2 2 2 4 4 5 6 8 0 4 6 5 5 2 3 2  250 0 0 0 4 2 0 4 0 0 4 4 1 0 3 0 3     3 4 5 8 0 3 4 4 4 0 0 1  125 0 0 0 0 0 0 2 0 0 3 4 0 0 0 0 3 0 3 4 6 0 2     4 2 0 0 0 0  64 -- 0 0 0 0 0 2 0 0 3 3 0 0 0 0 0 0 0 2 5 0 0 2 0 0 0 0 0      32 -- -- 0 0 0 -- 0 0 -- 2 0 -- -- -- 0 0 0 0 0 2 -- -- -- -- -- 0 0 --      16 -- -- -- -- -- -- 0 0 -- -- -- -- -- -- -- -- -- -- --  -- -- -- --     -- -- -- -- -- Umbrella Sedge 1000 -- 9 -- -- -- 10 -- -- 9 -- -- 10 10     10 -- -- -- -- -- -- 10 10 10 10 10 -- -- 10  500 9 9 10 10 10 9 -- -- 9     10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10  250 8 9 9 10 10     9 10 10 9 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10  125 0 8     9 10 10 0 10 10 9 9 10 10 9 10 9 10 10 10 10 10 10 10 10 10 9 9 9 9  64     -- 7 9 9 10 0 10 9 8 9 10 9 9 10 8 10 10 10 10 10 9 10 9 9 9 9 8 9  32     -- -- 6 6 5 -- 10 7 -- 8 10 -- -- -- 5 10 9 10 9 10 -- -- -- -- -- 9 5     --  16 -- -- -- -- -- -- 9 6 -- -- -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- -- -- -- Waterchestnut 1000 -- 8 -- -- -- 5 -- -- 7 -- -- 9 6 9     10 -- -- -- -- -- 9 7 4 9 9 -- -- 3  500 5 10 8 5 5 4 -- -- 6 6 8 6 10 4     4 7 2 9 9 10 4 8 4 7 9 8 7 3  250 0 10 5 5 5 0 5 4 5 5 5 5 8 0 0 5 0 9     10 9 3 7 7 9 8 7 2 --  125 0 8 0 5 4 0 4 0 0 5 0 0 0 0 0 0 0 9 8 9 0 7 0     9 7 4 0 --  64 -- 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 10 4 9 0 -- 0 0 5 0 0     --  32 -- -- 0 0 0 -- 0 0 -- 0 0 -- -- -- 0 0 0 10 4 9 -- -- -- -- -- 0     0 --  16 -- -- -- -- -- -- 0 0 -- -- -- -- -- -- -- -- -- -- -- -- -- --     -- -- -- -- -- --

TEST D

Seeds of spring and winter barley (Hordeum vulgare), black nightshade(Solanum nigrum), blackgrass (Alopecurus myosuroides), bluegrass (Poaannua), catchweed bedstraw (Galium aparine), cheatgrass (Bromussecalinus(), downy brome (Bromus tectorum), field pennycress (Thlaspiarvense), field violet (Viola arvensis), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum), ivyleaf speedwell(Veronica hederaefolia), jointed goatgrass (Aegilops cylindrica), kochia(Kochia scroparia), lambsquarters (Chenopodium album), Persian speedwell(Veronica persica), rape (Brassica napus), Russian thistle (Salsolakali), scentless chamomile (Matricaria inordora), sugar beet (Betavulgaris), spring and winter wheat (Triticum aestivum), wild buckwheat(Polygonum convolvulus), and wild oat (Avena fatua) were planted andtreated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. Postemergence applications of test chemicals were also appliedto these same crop and weed species. Plants ranged in height from two totwenty-four cm (two to three leaf stage) for postemergence treatments.Blackgrass and wild oat were treated postemergence at two growthstages--the first stage being at two to three leaves and the secondstage being approximately at four leaves or in the initial stages oftillering. Treated plants and controls were maintained in a greenhousefor approximately 21 days, after which all species were compared tocontrols and visually evaluated. Rates of application of each compoundare listed in Table D. Plant response ratings, summarized in Table D,are based on a scale of 0 to 10 where 0 is no effect and 10 is completecontrol. A dash (-) response means no test result.

    TABLE D      POSTEMERGENCE COMPOUND (1000 g/ha) COMPOUND (750 g/ha)  4 9 13 20 23 25 2     8 32 33 36 37 4044 46 50 82 4 9 13 15 20 23 25 28 32 36 37 40 44 46 49     50 53 55 82       Barley (Spring) 0 0 0 1 4 2 1 2 3 6 2 1 2 2 8 1 0 0 0 3 1 3 2 1 2 3 2     1 1 1 2 8 7 4 1 Barley (Winter) 0 0 0 1 3 2 1 2 2 5 2 2 1 2 7 1 0 0 0 2     1 3 1 0 2 2 2 1 1 1 2 6 6 2 1 Black nightshade 0 1 0 10 10 10 7 10 10 10     10 8 10 9 10 10 0 1 0 8 6 10 9 7 10 10 10 8 10 7 3 10 9 7 7 Blackgrass 0     0 0 4 9 3 4 4 4 9 8 3 8 7 10 4 0 0 0 8 4 9 3 1 4 9 8 3 5 7 2 10 9 8 1     Blackgrass (Stage 2) 0 0 0 2 6 2 1 5 4 9 7 1 3 5 8 2 0 0 0 2 2 4 2 1 2 8     3 1 3 4 2 8 9 7 2 Bluegrass 0 1 0 4 9 8 3 9 9 10 9 9 9 10 10 10 0 0 0 7     2 9 6 1 9 9 8 9 8 10 1 10 10 10 9 Catchweed bedstraw 0 0 0 3 7 6 4 9 5 9     3 3 5 4 2 2 0 0 0 3 3 5 4 4 6 4 3 3 5 2 2 2 7 3 1 Cheatgrass 0 0 0 1 5 2     1 2 1 8 4 2 2 4 8 1 0 0 0 1 0 3 1 0 2 7 2 1 2 4 0 8 8 4 0 Downy brome 0     0 0 0 2 2 1 3 1 2 3 1 1 1 5 1 0 0 0 1 0 2 1 0 1 2 3 1 0 1 0 4 8 2 0     Field pennycress 0 4 8 10 10 10 8 10 10 10 10 10 10 10 10 10 0 1 7 10 10     10 10 8 10 10 10 10 10 10 10 10 10 10 10 Field violet 0 2 4 10 10 10 10     10 10 10 10 10 10 9 10 10 0 2 1 10 8 10 10 6 10 10 10 10 10 9 3 10 10 10     10 Green foxtail 2 2 1 7 10 9 10 10 10 10 10 9 10 10 10 10 0 0 0 10 6 10     9 7 9 10 10 9 10 10 9 10 10 10 10 Italian ryegrass 0 0 0 1 9 5 1 4 1 9 4     2 2 8 10 2 0 0 0 2 1 8 2 0 3 8 3 2 2 4 1 9 9 8 2 Ivyleaf speedwell 0 2 3     8 10 10 9 10 10 10 10 10 10 10 10 10 0 2 3 8 7 10 10 7 10 10 10 10 10 10     2 10 8 10 10 Jointed goatgrass 0 0 0 1 3 2 1 2 2 3 3 1 2 1 5 1 0 0 0 2 1     2 2 0 1 3 2 1 1 1 1 4 5 4 0 Kochia 0 2 10 9 9 9 10 10 10 10 10 10 10 10     10 10 0 1 6 10 8 9 9 10 8 10 10 10 10 10 8 10 -- 9 10 Lambsquarters 0 2     2 5 10 10 3 10 10 10 10 10 8 10 10 10 0 2 2 7 5 10 10 3 10 10 10 10 7 9     2 10 8 8 10 Persian speedwell 0 1 5 9 10 10 10 10 10 10 10 4 10 9 9 9 0     1 5 7 9 10 10 10 10 8 10 4 10 9 4 9 9 8 7 Rape 3 6 7 7 10 10 9 10 10 10     10 9 8 9 10 10 0 6 2 8 7 10 9 7 10 10 10 8 6 9 6 10 10 10 8 Russian     thistle 0 0 1 4 8 8 5 7 8 9 9 9 9 9 9 9 0 0 0 5 2 8 8 2 7 9 9 9 8 9 4 9     9 9 8 Scentless chamomile -- -- 0 0 0 0 1 1 1 2 2 1 1 1 2 1 -- -- 0 0 0     0 0 0 0 2 2 1 1 1 -- 1 8 2 0 Sugar beet 2 9 8 10 10 10 5 10 10 10 10 8     10 10 10 10 1 8 8 10 10 10 10 5 10 10 10 7 10 10 9 10 10 10 10 Wheat     (Spring) 0 0 0 0 3 2 1 1 2 3 2 1 1 2 6 1 0 0 0 2 0 3 2 1 1 3 1 1 1 2 2 2     6 3 1 Wheat (Winter) 0 0 0 0 4 1 1 1 1 6 1 1 1 3 7 1 0 0 0 2 0 3 1 1 1 3     1 1 1 2 2 3 6 3 1 Wild buckwheat 0 1 1 3 9 10 5 10 9 9 9 2 7 9 10 7 0 1     0 7 1 8 9 2 9 9 9 2 3 7 2 10 9 10 5 Wild oat 0 0 0 2 6 4 1 4 3 9 8 3 2 5     8 2 0 0 0 2 2 6 4 0 4 8 8 3 2 4 2 8 9 8 2 Wild oat (Stage 2) 0 0 0 1 8 3     1 4 4 9 6 2 3 4 8 3 0 0 0 2 1 6 2 0 3 7 6 2 2 3 1 8 8 8 1       COMPOUND (500 g/ha) COMPOUND (250 g/ha)  4 5 9 13 15 20 23 25 28 32 33 3     6 37 40 44 46 48 49 50 53 55 56 57 71 73 7682 84 100 4 5 9 13 15 20     23     Barley (Spring) 0 2 0 0 2 0 2 1 0 2 1 3 1 1 1 1 2 2 4 3 3 2 5 4 3     3 1 3 3 0 1 0 0 2 0 2 Barley (Winter) 0 1 0 0 2 1 2 1 0 1 1 2 1 1 0 1 2     1 5 3 2 2 3 4 1 3 1 3 3 0 0 0 0 1 0 1 Black nightshade 0 5 0 0 7 4 10 7     4 10 6 10 6 7 6 5 7 3 10 9 7 8 10 6 10 10 7 10 10 0 2 0 0 5 2 6 Blackgras     s 0 0 0 0 6 2 3 1 1 4 1 8 7 2 3 5 4 2 8 9 7 1 4 6 3 3 1 8 7 0 0 0 0 2 0     1 Blackgrass (Stage 2) 0 0 0 0 2 1 2 1 0 1 2 4 3 1 1 2 2 2 7 8 5 2 2 3 3     1 1 5 4 0 0 0 0 1 1 1 Bluegrass 0 1 0 0 5 1 7 4 0 8 6 9 8 9 8 9 4 1 10     10 9 2 10 10 9 10 8 10 2 0 0 0 0 2 0 3 Catchweed bedstraw 0 0 0 0 1 2 5     3 4 6 2 4 2 2 4 2 5 1 2 4 2 2 8 6 8 6 0 9 9 0 0 0 0 1 0 4 Cheatgrass 0 1     0 0 0 0 1 0 0 1 1 3 1 1 1 2 2 0 7 8 3 3 4 5 1 2 0 4 3 0 1 0 0 0 0 1     Downy brome 0 1 0 0 0 0 1 0 0 1 1 1 1 1 0 0 2 0 2 6 1 3 2 3 1 3 0 3 3 0     1 0 0 0 0 1 Field pennycress 0 3 1 5 10 8 10 10 4 10 10 10 10 10 10 10     10 7 10 10 10 9 10 8 10 10 10 10 10 0 1 1 2 9 3 10 Field violet 0 10 2 0     10 7 10 10 5 7 10 9 10 10 8 9 9 2 10 9 10 6 10 10 6 10 10 10 10 0 10 1 0     8 5 10 Green foxtail 0 0 0 0 8 4 10 9 3 8 9 10 10 9 10 10 10 9 10 10 10     7 10 10 10 10 8 10 9 0 0 0 0 8 4 10 Italian ryegrass 0 1 0 0 2 0 7 1 0 1     1 3 1 1 1 4 2 0 7 9 7 3 9 3 8 3 1 10 9 0 0 0 0 1 0 3 Ivyleaf speedwell 0     7 1 1 8 6 10 10 9 10 9 10 10 7 10 7 8 1 10 8 10 10 9 10 9 10 9 10 10 0 7     0 0 8 4 10 Jointed goatgrass 0 0 0 0 2 0 2 1 0 0 2 3 1 1 1 1 1 0 2 3 2 1     3 2 0 2 0 3 1 0 0 0 0 1 0 1 Kochia 0 8 0 -- 8 8 9 9 10 8 10 10 10 10 10     10 8 8 7 8 9 7 9 7 7 8 10 9 9 0 7 0 2 5 6 8 Lambsquarters 0 4 0 1 7 3 10     10 3 10 9 10 9 9 4 8 9 2 8 8 7 4 10 6 2 9 9 10 10 0 4 0 1 7 1 9 Persian     speedwell 0 7 0 2 7 7 9 10 10 10 9 8 10 4 9 7 9 2 9 9 7 8 9 10 9 10 7 10     10 0 7 0 0 6 6 9 Rape 0 3 2 1 8 6 10 9 7 9 10 10 9 6 6 8 7 6 10 10 9 8     10 7 8 9 8 9 8 0 3 2 1 7 5 8 Russian thistle 0 4 0 0 4 1 8 8 2 7 8 9 9 9     8 8 7 1 9 9 9 1 7 6 1 10 8 8 7 0 4 0 0 4 1 6 Scentless chamomile 0 0 --     0 1 0 0 0 0 0 0 1 1 1 1 0 0 0 1 -- -- 1 1 2 0 5 0 1 2 0 0 0 0 0 0 0     Sugar beet 1 8 7 7 9 9 10 10 5 10 9 10 10 7 10 10 10 9 10 10 10 8 10 10     10 10 10 10 10 0 7 6 6 9 8 10 Wheat (Spring) 0 0 0 0 2 0 2 1 0 1 2 3 1 1     1 1 1 2 2 5 3 2 3 2 3 3 1 2 2 0 0 0 0 2 0 1 Wheat (Winter) 0 0 0 0 2 0 1     1 0 0 1 2 0 0 0 1 1 2 2 5 3 2 3 2 2 2 1 2 2 0 0 0 0 2 0 1 Wild buckwheat     0 6 0 0 7 1 7 8 1 9 8 8 9 2 2 6 2 2 10 7 8 6 3 4 2 6 2 8 8 0 5 0 0 2 0 3     Wild oat 0 1 0 0 1 1 5 3 0 3 1 8 4 2 2 1 3 1 5 8 6 3 4 3 4 4 1 7 5 0 1 0     0 1 1 3 Wild oat (Stage 2) 0 1 0 0 2 1 5 2 0 3 4 6 3 2 1 2 2 1 7 7 4 2 4     3 4 3 0 8 2 0 1 0 0 1 0 2       COMPOUND (250 g/ha) COMPOUND (125 g/ha)  25 28 32 333637 4044 45 46 48 4     9 50 53 55 5657 71 73 7476 82 84100 45 913 15 20 23 25 28 32 33 36       Barley (Spring) 1 0 1 1 1 1 1 1 0 0 2 1 1 3 3 2 3 3 2 2 2 1 3 2 0 0 0     0 2 0 1 0 0 0 0 0 Barley (Winter) 0 0 1 1 1 1 1 0 0 0 2 0 2 2 2 1 3 2 1     1 2 0 1 2 0 0 0 0 1 0 1 0 0 0 1 0 Black nightshade 7 2 7 6 10 6 5 6 2 4     5 3 8 6 6 5 10 4 7 10 7 2 10 10 0 1 0 0 5 1 5 3 0 7 3 10 Blackgrass 1 0     2 1 6 5 1 1 2 5 2 1 6 8 7 0 4 2 2 3 2 0 8 5 0 0 0 0 1 0 1 0 0 1 0 3     Blackgrass (Stage 2) 0 0 1 1 2 1 1 1 1 1 1 1 2 5 2 2 2 2 1 2 1 0 2 2 0 0     0 0 1 0 1 0 0 0 0 1 Bluegrass 2 0 3 3 8 3 7 2 1 8 4 0 9 10 8 1 9 9 7 2 8     3 9 1 0 0 0 0 1 0 1 0 0 1 2 6 Catchweed bedstraw 1 1 6 1 4 2 2 4 0 1 5 0     1 3 1 2 8 4 7 3 6 0 9 9 0 0 0 0 1 0 4 0 0 5 0 4 Cheatgrass 0 0 0 0 1 1 1     1 0 2 2 0 4 3 3 3 4 3 1 1 2 0 2 1 0 0 0 0 0 0 0 0 0 0 0 0 Downy brome 0     0 0 0 0 0 1 0 0 0 2 0 1 2 1 3 2 1 0 1 1 0 2 1 0 0 0 0 0 0 1 0 0 0 0 0     Field pennycress 10 1 10 8 10 10 10 8 8 8 6 7 9 10 10 3 8 7 4 8 7 7 10 7     0 0 1 0 8 0 3 6 0 9 5 10 Field violet 10 4 5 9 9 10 8 7 3 7 7 2 8 9 7 6     10 6 3 10 10 9 10 10 0 6 0 0 2 2 4 2 1 3 8 3 Green foxtail 8 1 6 8 8 7 7     8 7 6 7 7 9 10 10 4 10 10 9 7 7 4 10 9 0 0 0 0 6 1 7 5 0 5 5 8 Italian     ryegrass 0 0 1 0 3 0 1 1 0 1 1 0 2 8 2 3 7 1 2 4 1 0 9 7 0 0 0 0 1 0 1 0     0 0 0 1 Ivyleaf speedwell 10 6 10 9 10 10 7 10 2 4 8 1 9 8 9 10 9 10 9     10 10 7 10 10 0 7 0 0 7 2 9 3 2 9 8 9 Jointed goatgrass 0 0 0 0 1 0 0 0     0 1 1 0 0 1 2 1 1 2 0 1 1 0 1 1 0 0 0 0 1 0 1 0 0 0 0 0 Kochia 9 10 8 10     10 9 9 10 -- 9 7 8 5 -- 6 4 8 7 6 8 7 10 9 9 0 4 0 0 5 5 8 7 6 7 8 10     Lambsquarters 8 1 10 5 10 6 8 4 2 7 4 1 2 8 4 4 10 3 2 3 7 8 9 9 0 2 0 0     5 0 4 2 0 10 5 6 Persian speedwell 10 9 10 4 7 9 2 7 2 6 8 2 7 8 7 8 9 9     9 8 10 6 10 10 0 7 0 0 3 3 7 5 1 9 3 6 Rape 7 5 9 8 10 8 6 5 4 8 6 4 7 9     8 6 9 4 8 6 7 7 8 8 0 1 1 0 7 3 5 5 2 8 6 4 Russian thistle 6 1 6 7 9 8     9 6 2 8 7 1 4 8 7 0 5 4 0 2 10 7 5 7 0 4 0 0 3 0 4 2 0 6 5 9 Scentless     chamomile 0 0 0 0 1 1 1 0 2 0 0 -- 0 5 -- 0 1 0 0 5 1 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 Sugar beet 10 5 10 9 10 10 7 9 9 10 8 7 10 10 9 4 10 9 8 9     10 10 10 9 0 5 6 2 8 7 8 8 4 9 9 9 Wheat (Spring) 0 0 0 1 1 0 1 1 1 0 1     1 1 5 3 1 1 2 3 2 2 1 2 2 0 0 0 0 2 0 1 0 0 0 1 1 Wheat (Winter) 0 0 0 0     1 0 0 0 1 1 1 1 1 3 2 1 2 2 2 1 2 0 2 2 0 0 0 0 2 0 1 0 0 0 0 1 Wild     buckwheat 4 0 7 6 4 9 2 2 1 5 1 1 10 3 3 2 0 4 2 5 4 1 7 7 0 3 0 0 2 0 1     2 0 7 6 2 Wild oat 1 0 1 1 6 4 2 1 1 1 3 0 3 5 4 2 2 3 2 1 3 1 7 4 0 1 0     0 1 0 1 0 0 0 1 3 Wild oat (Stage 2) 1 0 1 2 2 2 1 1 2 1 2 0 4 4 2 2 3 3     2 2 3 0 6 1 0 1 0 0 1 0 1 0 0 0 1 2       COMPOUND (125 g/ha) COMPOUND (64 g/ha)  37 40 44 45 46 48 49 50 53 55     56 57 71 73 74 76 82 84 100 4 5 9 13 15 20 23 32 33 36 37 40  44 45 46     48 49       Barley (Spring) 1 0 0 0 0 2 0 0 2 2 1 3 3 2 1 2 0 2 2 0 0 0 0 1 0 1 0     0 0 0 0 0 0 0 1 0 Barley (Winter) 0 1 0 0 0 2 0 1 2 2 0 3 2 0 1 0 0 1 2     0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 1 0 Black nightshade 6 5 3 2 4 2 1 3 5 5 1     2 2 7 7 3 1 10 7 0 0 0 0 3 0 5 1 1 2 2 5 2 1 2 0 0 Blackgrass 2 1 1 0 2     2 0 3 6 6 0 2 0 0 1 1 0 1 5 0 0 0 0 0 0 0 0 0 1 0 0 0 0 1 1 0 Blackgrass     (Stage 2) 0 0 0 1 0 1 1 1 1 2 1 2 1 1 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0     0 0 0 0 0 Bluegrass 2 3 1 0 8 2 0 6 7 5 0 3 2 2 1 5 1 2 1 0 0 0 0 0 0 1     0 0 2 0 0 0 0 6 1 0 Catchweed bedstraw 1 2 2 0 0 3 0 0 1 1 1 7 3 5 1 4 0     6 8 0 0 0 0 0 0 3 1 0 1 0 1 0 0 0 2 0 Cheatgrass 0 1 1 0 1 2 0 2 3 1 1 2     1 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 1 0 Downy brome 0 0 0 0 0 1     0 0 2 0 1 2 1 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Field     pennycress 9 10 3 2 6 2 3 6 9 8 0 5 3 2 8 5 4 10 3 0 0 1 0 2 0 2 3 2 4 4     3 3 0 2 0 3 Field violet 4 7 3 2 5 7 1 4 9 2 5 7 6 2 7 9 7 6 4 0 4 0 0 1     0 2 0 3 2 24 1 2 2 4 1 Green foxtail 7 5 2 7 3 6 6 9 9 10 1 8 8 5 2 2 2     10 8 0 0 0 0 2 0 6 2 2 5 0 2 1 5 2 3 2 Italian ryegrass 0 0 1 0 0 1 0 1     7 1 1 4 1 1 1 1 0 3 2 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Ivyleaf speedwell      5 6 10 2 2 6 0 7 7 8 5 7 10 7 9 9 5 10 10 0 7 0 0 2 0 9 5 8 8 3 2 1 1 0     6 0 Jointed goatgrass 0 0 0 0 0 0 0 0 1 1 0 0 1 0 0 1 0 1 0 0 0 0 0 0 0     1 0 0 0 0 0 0 0 0 0 0 Kochia 9 9 10 0 7 7 2 1 2 -- 2 6 5 6 8 7 10 8 6 0     4 0 0 0 5 7 6 6 8 7 8 8 0 5 5 0 Lambsquarters 3 6 2 2 5 2 0 0 7 3 1 6 2     0 3 7 5 7 6 0 2 0 0 2 0 4 2 0 3 1 3 1 1 3 1 0 Persian speedwell 3 2 4 2     3 6 2 7 8 6 7 8 8 7 7 9 3 10 8 0 6 0 0 2 0 5 3 0 3 2 1 2 2 1 3 2 Rape 8     2 2 2 7 4 3 6 8 7 3 7 2 4 3 7 3 7 7 0 0 0 0 5 1 5 6 3 1 2 1 0 1 5 3 1     Russian thistle 8 8 3 1 7 3 0 -- 6 5 0 4 2 0 2 7 4 3 4 0 1 0 0 1 0 2 4 3     8 5 5 1 0 5 1 0 Scentless chamomile 0 1 0 0 0 0 -- 0 5 -- 0 0 0 0 2 0 0     0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 -- 0 0 -- Sugar beet 10 7 9 8 9 7 7 7 9 9     3 9 8 7 9 9 9 10 9 0 2 2 0 7 4 7 6 8 9 8 6 7 6 7 5 6 Wheat (Spring) 0 0     0 0 0 1 1 0 4 2 0 1 1 1 1 1 0 1 2 0 0 0 0 1 0 1 0 0 1 0 0 1 0 0 0 0     Wheat (Winter) 0 0 0 0 0 1 0 0 2 2 1 1 1 1 1 1 0 1 1 0 0 0 0 1 0 1 0 0 0     0 0 0 0 0 0 0 Wild buckwheat 2 2 0 0 3 0 1 4 1 1 1 0 2 1 2 0 0 6 2 0 0 0     0 0 0 0 2 4 0 0 0 0 0 1 0 0 Wild oat 2 1 1 0 0 2 0 1 2 2 2 2 3 2 1 2 0 3     2 0 1 0 0 1 0 1 0 0 2 1 1 0 0 0 1 0 Wild oat (Stage 2) 1 1 1 1 1 2 0 1 3     2 1 2 1 2 1 2 0 2 1 0 0 0 0 0 0 1 0 0 1 1 0 0 0 0 1 0       COMPOUND (64 g/ha) COMPOUND (32 g/ha)  50 53 55 56 57 71 73 74 76 82     84 100 5 13 23 46 48 56 57 71 73 74 76 82 100       Barley (Spring) 0 1 1 0 2 3 1 0 1 0 2 1 0 0 1 0 0 0 2 3 0 0 1 0 1     Barley (Winter) 0 1 1 0 2 2 0 0 0 0 1 1 0 0 1 0 0 0 1 1 0 0 0 0 1 Black     nightshade 0 4 2 0 2 2 5 5 3 0 6 7 0 0 2 0 0 0 1 0 1 2 2 0 3 Blackgrass     0 2 4 0 2 0 0 0 1 0 1 2 0 0 0 0 0 0 1 0 0 0 0 0 0 Blackgrass (Stage 2) 0     0 1 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Bluegrass 1 2 2 0 3 2 1     0 3 0 1 0 0 0 0 2 0 0 1 0 0 0 1 0 0 Catchweed bedstraw 0 0 0 0 2 3 2 0 2     0 3 7 0 0 1 0 0 0 0 1 1 0 0 0 3 Cheatgrass 0 1 0 0 1 0 0 0 0 0 1 0 0 0 0     0 0 0 0 0 0 0 0 0 0 Downy brome 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     0 0 0 0 0 Field pennycress 1 3 7 0 2 1 0 2 5 2 4 3 0 0 0 0 0 0 0 0 0 0 3     0 0 Field violet 0 6 2 3 7 3 2 4 9 3 4 2 2 0 1 0 1 0 3 1 1 1 3 1 0 Green     foxtail 6 9 7 0 6 5 1 0 2 0 8 6 0 0 4 0 2 0 2 2 0 0 0 0 2 Italian     ryegrass 0 2 1 0 2 0 1 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 Ivyleaf     speedwell 2 5 8 0 7 8 7 7 8 3 9 10 3 0 8 0 2 0 5 5 6 4 5 0 8 Jointed     goatgrass 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Kochia 0 0 1     2 3 3 4 7 5 8 8 4 1 0 4 2 2 1 1 1 2 3 3 5 3 Lambsquarters 0 2 2 0 2 2 0     0 3 2 4 4 0 0 2 0 0 0 0 0 0 0 2 0 3 Persian speedwell 3 4 5 4 6 5 6 3 7     1 6 8 1 0 4 0 0 2 4 2 3 0 4 0 6 Rape 2 6 7 1 4 2 2 1 5 2 6 7 0 0 2 0 0 0     4 1 1 0 3 0 4 Russian thistle 1 1 4 0 2 0 0 1 3 2 2 2 0 0 1 2 0 0 1 0 0     0 1 0 1 Scentless chamomile 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     0 0 0 Sugar beet 4 8 8 3 8 7 6 8 9 8 9 7 2 0 5 3 5 0 6 7 2 7 8 4 5 Wheat     (Spring) 0 1 2 0 1 1 1 0 1 0 1 1 0 0 1 0 0 0 0 0 0 0 0 0 1 Wheat     (Winter) 0 2 2 0 1 1 0 0 1 0 1 1 0 0 1 0 0 0 1 0 0 0 0 0 1 Wild buckwheat      1 0 1 0 0 1 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild oat 0 1 1 1 2 2     1 0 2 0 2 2 0 0 1 0 0 0 2 2 1 0 1 0 1 Wild oat (Stage 2) 0 1 1 1 2 1 1 1     2 0 1 1 0 0 0 0 1 0 1 1 1 0 0 0 1       PREEMERGENCE COMPOUND (1000 g/ha) COMPOUND (750 g/ha)  4 9 13 20 23 25 2     8 32 33 36 37 40 44 46 50 82 4 9 13 15 20 23 25 28 32 36 37 40 44 46 49     50 53 55 82       Barley (Spring) 0 1 3 2 4 2 1 3 1 5 3 2 5 3 6 3 0 0 2 1 1 3 2 1 2 5 3     2 4 3 2 6 10 7 3 Barley (Winter) 0 1 2 2 2 3 1 1 1 4 2 1 3 4 6 2 0 0 0 0     1 2 2 1 1 3 2 0 3 4 2 6 7 5 1 Black nightshade 0 7 10 10 10 10 8 10 10     10 9 10 10 10 10 10 0 7 10 10 10 10 10 8 10 10 9 10 10 10 9 10 10 10 10     Blackgrass 1 3 10 10 10 10 9 10 10 10 10 10 10 10 10 10 1 3 10 10 10 10     10 7 10 10 10 10 10 10 7 10 10 10 10 Bluegrass 0 1 10 10 10 10 10 10 10     10 10 10 10 10 10 10 0 1 10 10 10 10 10 10 10 10 10 9 10 10 9 10 10 10     10 Catchweed bedstraw 0 2 0 4 10 10 3 10 7 10 8 9 8 10 10 3 0 1 0 7 2 10     7 1 10 10 8 9 8 4 2 10 10 7 3 Cheatgrass 0 0 3 2 10 6 1 5 1 10 10 3 7 9     10 2 0 0 2 8 2 8 5 0 2 10 9 3 4 9 3 10 10 10 2 Downy brome 0 0 8 2 10 6     1 3 1 9 7 2 6 6 10 4 0 0 5 7 2 8 3 1 3 8 5 2 3 4 0 7 10 7 2 Field     pennycress 2 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 1 10 10 10 10     10 10 10 10 10 10 10 10 10 10 10 10 10 10 Field violet 1 10 10 10 10 10     10 10 10 10 10 10 10 10 10 10 0 10 10 10 10 10 10 9 10 10 10 10 10 10 10     10 10 10 10 Green foxtail 2 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10     1 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 Italian ryegrass     0 3 9 9 10 6 3 10 6 10 10 9 9 10 10 9 0 2 7 9 7 10 2 3 3 10 10 9 9 10 4     10 10 10 9 Ivyleaf speedwell 0 8 10 10 10 10 10 10 10 10 10 10 10 10 10     10 0 4 10 10 10 10 10 10 10 10 10 8 10 10 9 10 10 10 10 Jointed goatgrass      0 0 2 2 2 3 1 3 2 4 4 4 2 3 7 1 0 0 1 2 0 1 1 0 3 4 4 1 2 2 3 4 6 8 1     Kochia 0 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 0 9 10 10 9 10 10     10 10 10 10 10 10 10 10 10 10 10 10 Lambsquarters 1 9 10 10 10 10 10 10     10 10 10 10 10 10 10 10 0 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10     10 10 Persian speedwell 0 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 0     8 10 10 10 10 10 10 10 10 10 10 10 10 9 10 10 10 10 Rape 1 9 10 10 10 10     10 10 10 10 10 10 10 10 10 10 1 6 10 10 10 10 10 10 10 10 10 10 10 10 10     10 10 10 10 Russian thistle 0 4 10 8 10 10 2 9 10 10 8 8 9 10 10 10 0 2     10 10 3 10 10 2 9 10 8 8 9 8 2 10 10 10 7 Scentless chamomile 1 3 10 10     8 10 10 10 8 10 10 9 9 10 10 10 -- 3 8 10 9 6 9 9 9 9 9 9 9 10 10 10 10     10 10 Sugar beet 2 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 1 10 10     10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 Wheat (Spring) 0 1 3 2 4     2 1 2 1 4 3 0 3 3 5 2 0 0 1 3 2 3 1 0 2 2 3 0 3 2 3 5 8 6 2 Wheat     (Winter) 0 1 1 2 4 1 1 4 1 4 2 0 2 5 6 3 0 0 1 4 1 3 1 0 1 4 1 0 2 2 2 5     9 4 1 Wild buckwheat 0 9 10 4 10 10 10 10 10 10 10 8 10 10 10 5 0 9 10     10 3 10 10 10 10 10 10 8 10 10 8 10 10 10 5 Wild oat 0 2 8 3 10 4 2 7 3     10 9 7 7 10 10 10 0 0 2 9 3 9 4 1 6 10 9 7 7 10 4 9 10 10 9       COMPOUND (500 g/ha) COMPOUND (250 g/ha)  4 5 9 13 15 202325 28 32 33     36 37 40 44 46 48 49 50 53 55 56 57 71 73 76 82 84 100 4 5 9 13 15 20     23   Barley (Spring) 0 0 0 1 0 1 1 1 0 1 1 4 2 1 1 3 2 0 5 7 3 2 5 2 5 3     1 6 1 0 0 0 1 0 0 1 Barley (Winter) 0 0 0 0 0 0 1 1 0 0 0 2 1 0 1 2 1 0     4 4 4 1 4 2 7 2 1 4 1 0 0 0 0 0 0 1 Black nightshade 0 10 7 510 10 10 10     7 10 10 10 9 10 10 7 7 9 10 10 10 10 10 10 10 8 10 10 10 0 9 2 5 10 10     10 Blackgrass 0 6 18 10 10 10 9 2 8 9 10 10 108 10 8 7 10 10 10 10 10 10     10 10 10 10 8 0 6 0 6 9 9 9 Bluegrass 0 8 110 10 10 9 10 9 10 10 10 10 9     10 10 10 9 10 10 10 8 10 10 10 10 10 9 10 0 2 0 10 8 9 9 Catchweed     bedstraw 0 0 0 0 3 1 10 4 1 7 3 10 7 9 5 4 10 1 3 10 5 10 10 10 10 10 2     10 10 0 0 0 0 1 1 8 Cheatgrass 0 2 0 1 6 1 7 1 0 2 1 9 9 2 2 4 5 2 10 10     8 5 10 10 10 2 1 9 2 0 0 0 0 5 0 2 Downy brome 0 0 0 2 4 1 7 3 0 1 0 8 5     2 1 2 2 0 7 9 7 5 10 10 7 7 1 6 2 0 0 0 1 1 0 2 Field pennycress 0 10 1     10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10     10 10 0 10 10 10 10 10 10 Field violet 0 10 9 10 10 10 10 9 9 9 10 10 10     10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 0 10 8 10 10 9 10 Green     foxtail 0 6 8 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10     10 10 10 10 10 10 10 0 2 3 10 10 10 10 Italian ryegrass 0 2 0 6 8 7 10 2     1 3 2 9 10 5 8 8 9 3 10 10 10 6 10 10 10 8 6 10 5 0 1 0 3 6 6 3 Ivyleaf     speedwell 0 10 2 10 10 10 10 10 10 9 9 10 10 8 10 10 10 7 10 10 10 10 10     10 10 10 10 10 10 0 9 0 5 10 9 10 Jointed goatgrass 0 0 0 0 1 0 1 0 0 1     0 2 2 1 1 1 1 3 2 6 5 0 8 3 3 1 0 3 2 0 0 0 0 0 0 0 Kochia 0 9 1 10 10 9     10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 10 9 9 10 10 10 10 0 9 0     10 10 8 10 Lambsquarters 0 10 8 10 10 9 10 10 910 10 10 9 9 10 10 10 10     10 10 10 10 10 10 10 10 10 10 10 0 8 8 10 10 7 10 Persian speedwell 0 10     7 10 10 10 10 10 10 10 10 10 10 10 10 10 10 7 10 10 10 10 10 10 10 10 10     10 10 0 10 5 10 10 8 10 Rape 0 10 6 8 10 9 10 10 9 10 10 10 10 10 10 10     10 10 10 10 10 9 10 10 10 10 9 10 10 0 8 4 6 10 8 10 Russian thistle 0 7     1 10 9 2 10 10 1 9 5 8 5 5 9 8 9 -- 8 10 9 7 6 3 9 10 3 10 10 0 2 1 10 7     1 10 Scentless chamomile 0 7 1 6 8 8 6 9 2 7 4 9 9 9 9 10 7 10 10 10 10     10 10 10 10 10 9 10 9 0 3 0 1 7 7 4 Sugar beet 0 10 10 10 10 10 10 10 9     10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 0 10 8 10 10     9 10 Wheat (Spring) 0 -- 0 1 1 1 3 1 0 1 0 2 1 0 1 2 2 2 5 8 3 2 5 2 7 1     1 5 1 0 0 0 0 0 0 2 Wheat (Winter) 0 0 0 1 0 0 1 0 0 1 0 3 1 0 2 1 2 2 3     9 3 2 4 2 6 0 1 4 0 0 0 0 0 0 0 1 Wild buckwheat 0 7 8 10 10 1 10 10 9     10 10 10 9 8 2 10 10 3 10 10 10 10 10 10 10 10 5 10 10 0 7 2 6 10 0 10     Wild oat 0 2 0 2 4 2 8 4 0 6 3 10 9 7 4 8 8 3 9 10 9 5 6 6 7 8 7 9 7 0 0     0 1 3 1 8       COMPOUND (250 g/ha) COMPOUND (125 g/ha)  25 28 32 33 36 37 40 44 45 46 4     8 49 50 53 55 56 57 71 73 74 76 82 84 100 4 5 9 13 15 20 23 25 28 32 33     36       Barley (Spring) 1 0 0 0 1 1 1 0 1 1 1 0 3 2 1 0 4 2 4 3 1 0 3 1 0 0 0     0 0 0 0 0 0 0 0 0 Barley (Winter) 0 0 0 0 1 1 0 0 0 1 0 0 2 4 1 1 4 2 5     4 1 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 Black nightshade 10 4 10 8 9 8 10 9 2     5 7 4 10 10 10 10 10 8 10 10 8 4 10 10 0 2 0 4 7 9 9 4 0 10 3 9 Blackgras     s 7 2 5 6 10 10 9 8 4 8 8 6 10 10 10 8 10 10 10 9 7 10 10 7 0 1 0 6 8 3     9 3 0 5 5 10 Bluegrass 10 3 10 9 10 10 9 9 2 10 8 3 10 10 10 3 10 10 10     10 10 8 9 7 0 0 0 9 6 6 9 8 10 10 8 10 Catchweed bedstraw 1 0 7 1 9 2 2     3 0 4 8 0 2 10 5 2 10 9 10 7 7 1 10 10 0 0 0 0 0 0 4 0 0 3 0 9 Cheatgrass      1 0 1 0 7 7 2 1 0 2 2 0 6 8 5 2 7 710 5 0 1 6 1 0 0 0 0 1 0 1 0 0 0 0 3     Downy brome 1 0 0 0 4 2 1 1 0 1 1 0 3 9 3 2 6 3 7 5 3 0 3 1 0 0 0 0 0 0     1 0 0 0 0 1 Field pennycress 10 7 10 10 10 10 10 10 10 10 9 10 10 10 10     10 10 10 10 10 9 10 10 10 0 9 10 7 10 10 10 9 5 9 10 10 Field violet 9 9     9 10 10 9 10 10 10 10 9 10 10 10 10 10 10 10 10 10 10 10 10 10 0 10 4 8     10 9 10 8 6 9 10 10 Green foxtail 10 10 10 10 10 10 10 10 10 10 10 9 10     10 10 10 10 10 10 10 10 10 10 10 0 0 3 10 10 9 10 9 10 10 10 10 Italian     ryegrass 2 0 2 1 9 9 4 6 1 8 6 1 80 10 10 3 9 8 9 9 7 2 8 5 0 0 0 1 3 2     3 2 0 1 0 9 Ivyleaf speedwell 9 3 9 9 10 9 8 10 3 10 10 3 10 10 10 10 10     10 10 10 10 5 10 10 0 0 0 2 4 3 10 8 0 9 8 10 Jointed goatgrass 0 0 1 0     1 1 0 0 0 0 1 1 1 4 4 0 3 1 1 2 0 0 3 1 0 0 0 0 0 0 0 0 0 0 0 1 Kochia 9     9 10 10 10 10 8 10 0 10 7 10 10 10 10 9 9 7 6 9 10 8 10 10 0 3 0 10 9 8     4 8 8 9 9 10 Lambsquarters 10 9 10 10 9 9 9 10 9 10 10 10 10 10 10 10 10     9 10 10 10 10 10 10 0 8 5 8 9 4 10 9 2 10 9 9 Persian speedwell 10 8 10     10 9 10 8 9 10 10 10 3 10 10 10 10 10 10 10 10 10 10 10 10 0 10 2 10 9 8     10 10 2 10 5 9 Rape 10 6 10 10 10 9 8 10 7 9 9 3 10 10 10 7 10 5 10 10 9     6 10 10 0 8 03 10 3 6 2 1 10 9 10 Russian thistle 7 0 8 4 8 5 5 5 5 4 3     0 4 8 8 2 3 1 3 9 10 1 10 10 0 0 0 7 3 0 9 6 0 7 3 4 Scentless chamomile     6 2 6 2 8 8 8 7 9 10 7 10 10 10 10 10 8 10 10 10 10 9 10 7 0 0 0 0 0 7 1     1 0 6 1 8 Sugar beet 10 7 10 10 10 10 10 10 10 9 10 10 10 10 10 10 10 10     10 10 10 9 10 10 0 10 5 6 10 9 10 6 5 10 9 10 Wheat (Spring) 0 0 1 0 1 1     0 1 0 1 0 0 5 5 1 0 4 2 6 3 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat     (Winter) 0 0 0 0 1 0 0 0 0 0 1 0 3 8 2 1 4 0 6 4 0 0 2 0 0 0 0 0 0 0 0 0     0 0 0 0 Wild buckwheat 9 9 10 10 10 9 7 2 1 4 9 0 9 10 9 10 10 10 7 10 7     2 10 10 0 2 1 1 8 0 9 9 5 9 9 4 Wild oat 2 0 2 1 9 8 3 2 1 6 5 1 8 10 6     2 6 6 7 3 4 4 8 5 0 0 0 0 2 1 2 1 0 1 0 8       COMPOUND (125 g/ha) COMPOUND (64 g/ha)  37 40 44 45 46 48 49 50 53 55     56 57 71 73 74 76 82 84 100 4 5 9 13 15 20 23 32 33 36 37 40 44 45 46 48 4     9       Barley (Spring) 0 0 0 0 1 0 0 1 2 0 0 2 1 3 1 1 0 1 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 0 0 Barley (Winter) 0 0 0 0 1 0 0 0 2 0 0 1 1 3 1 0 0 1 0     0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Black nightshade 4 8 9 0 -- 7 3 7 10 9     9 5 7 10 10 5 1 10 7 0 0 0 0 5 6 7 2 2 1 2 67 0 1 -- 0 Blackgrass 9 2 8     2 6 7 2 10 10 10 5 9 8 7 9 7 9 10 7 0 0 0 5 6 1 5 1 0 8 8 0 4 0 2 3 0     Bluegrass 9 9 9 0 7 4 2 9 10 10 1 10 9 9 8 7 3 8 2 0 0 0 8 2 4 2 7 5 9 8     7 6 0 3 1 0 Catchweed bedstraw 1 2 1 0 0 4 0 0 7 3 0 10 9 10 7 6 0 3 6 0     0 0 0 0 0 0 1 0 7 0 1 1 0 0 1 0 Cheatgrass 3 1 0 0 1 0 0 5 7 2 0 7 6 5 4     0 0 5 0 0 0 0 0 0 0 1 0 0 0 2 0 0 0 0 0 0 Downy brome 1 0 0 0 0 1 0 2 6     2 1 6 2 4 1 1 0 2 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Field pennycress     10 10 10 10 9 8 10 10 10 10 10 9 10 10 10 9 10 10 10 0 7 10 6 10 7 10 9     8 10 10 10 10 10 7 8 10 Field violet 9 10 9 10 10 9 9 10 10 7 10 10 10     10 10 9 10 10 9 0 2 2 3 10 3 10 7 7 8 9 7 8 3 10 8 3 Green foxtail 10 10     10 8 9 10 5 10 10 10 8 10 10 10 10 8 10 10 8 0 0 1 10 108 10 8 10 10 10     10 10 2 8 10 2 Italian ryegrass 7 4 6 0 3 3 0 5 9 9 1 8 7 7 7 3 1 6 4 0     0 0 0 1 0 2 0 0 5 4 1 1 0 1 1 0 Ivyleaf speedwell 9 8 10 1 3 8 0 10 10     10 3 9 10 10 10 10 1 10 10 0 0 0 0 2 1 9 8 6 10 7 74 0 1 7 0 Jointed     goatgrass 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0     0 0 0 0 0 Kochia 10 8 10 0 8 5 9 9 10 10 8 7 6 3 9 6 3 9 9 0 0 0 7 7 7 1     7 9 8 10 5 10 0 4 4 6 Lambsquarters 5 8 9 9 8 10 10 8 10 10 10 10 7 10     10 7 7 10 9 0 3 2 6 8 3 9 9 7 2 2 1 8 6 2 5 8 Persian speedwell 7 8 8 10     10 10 1 10 10 10 9 10 10 10 10 10 10 10 10 0 2 0 10 8 3 10 9 2 8 7 7 2 7     10 7 0 Rape 9 8 9 1 3 5 1 8 10 9 5 10 5 7 10 7 6 7 10 0 8 0 1 7 0 6 7 5     9 8 3 1 0 1 3 0 Russian thistle 3 2 2 4 2 1 0 3 8 6 2 2 0 1 6 6 1 9 7 0     0 0 2 1 0 2 4 1 2 1 1 1 0 0 0 0 Scentless chamomile 2 6 3 2 10 3 9 10 10     10 7 6 10 9 10 7 8 10 4 0 0 0 0 0 4 0 3 0 2 1 1 2 0 3 3 0 Sugar beet 10     9 8 1 9 10 9 10 10 10 10 10 10 10 10 10 6 10 10 0 10 2 6 10 8 10 9 8 9 4     8 7 1 8 8 7 Wheat (Spring) 0 0 0 0 0 0 0 2 5 0 0 2 0 2 3 0 0 2 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat (Winter) 0 0 0 0 0 0 0 1 5 0 0 1 0 4 2 0     0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild buckwheat 6 3 1 0 1 2 0 3     10 3 5 10 8 7 9 6 1 10 8 0 0 0 0 7 0 5 2 3 2 6 0 0 0 1 0 0 Wild oat 7 2     2 0 2 3 0 4 9 5 1 6 5 5 2 2 1 8 5 0 0 0 0 1 0 1 0 0 5 2 1 1 0 0 1     0        COMPOUND (64 g/ha) COMPOUND (32 g/ha)  50 53 55 56 57 71 73 74     76 82 84 100 5 13 23 46 48 56 57 71 73 74 76 82 100       Barley (Spring) 0 0 0 0 2 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     Barley (Winter) 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Black     nightshade 3 5 5 7 2 6 7 10 4 0 10 5 0 0 5 0 0 2 2 2 2 4 1 0 1 Blackgrass      8 9 8 1 5 5 7 7 4 4 7 6 0 4 1 0 1 0 2 3 1 4 2 0 4 Bluegrass 4 10 5 0 7     9 5 4 5 1 7 1 0 8 0 1 0 0 3 2 2 1 2 0 0 Catchweed bedstraw 0 2 0 0 8 1     10 4 2 0 0 1 0 0 0 0 0 0 7 0 7 1 0 0 0 Cheatgrass 1 3 1 0 3 2 2 2 0 0 2     0 0 0 0 0 0 0 1 0 1 0 0 0 0 Downy brome 0 2 0 0 1 0 3 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 0 0 Field pennycress 10 10 10 7 7 9 10 10 9 8 9 10 3 6 7 2     2 5 7 4 10 10 8 5 9 Field violet 5 10 7 10 10 10 8 9 9 10 10 9 1 0 9 0 8     7 8 8 7 48 3 8 Green foxtail 5 10 10 6 10 10 10 9 8 9 10 6 0 5 2 8 8 2 9     7 7 7 5 2 4 Italian ryegrass 3 6 6 0 5 2 6 5 1 0 4 2 0 0 0 0 0 0 2 0 1 1     0 0 0 Ivyleaf speedwell 2 10 9 3 9 4 10 10 8 0 10 10 0 0 7 0 3 0 3 2 4 8     3 0 9 Jointed goatgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     0 Kochia 7 10 9 3 5 2 3 7 4 0 7 7 0 6 0 0 0 0 2 0 1 5 1 0 3 Lambsquarters      8 9 9 9 9 7 10 10 7 2 10 8 0 0 7 0 2 6 6 2 9 9 4 0 4 Persian speedwell     9 10 10 9 10 7 10 10 10 10 10 9 0 0 8 3 2 7 8 7 8 10 6 0 8 Rape 4 9 9 3     5 3 4 10 7 3 6 8 3 0 2 0 0 1 2 0 1 2 5 0 6 Russian thistle 1 5 2 1 2 0 0     4 4 0 5 3 0 0 0 0 0 0 0 0 0 2 1 0 0 Scentless chamomile 10 4 3 3 6 5 7     10 4 5 7 4 0 0 0 1 0 1 2 2 2 7 1 2 0 Sugar beet 9 10 10 9 9 9 10 10 10 5     10 8 6 6 10 6 3 68 6 7 10 7 3 4 Wheat (Spring) 0 3 0 0 1 0 2 1 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 0 Wheat (Winter) 0 2 0 0 0 0 3 1 0 0 0 0 0 0 0 0 0     0 0 0 1 0 0 0 0 Wild buckwheat 0 8 2 2 7 3 2 9 4 0 8 7 0 0 2 0 0 0 1 0 0     3 2 0 2 Wild oat 2 7 2 0 5 4 2 2 1 0 5 1 0 0 0 0 0 0 2 2 1 0 0 0

TEST E

Seeds selected from barnyardgrass (Echinochloa crus-galli), bermudagrass(Cynodon dactylon), cocklebur (Xanthium pensylvanicum), cotton(Gossypium hirsutum), fall panicum (Panicum dichotomiflorum), goosegrass(Eleusine indica), ground cherry (Physalis heterophylla), johnsongrass(Sorghum halepense), lambsquarters (Chenopodium album), large crabgrass(Digitaria sanguinalis), morningglory (Ipomoea hederacea), purslane(Portulaca oleracea), redroot pigweed (Amaranthus retroflexus),sicklepod (Cassia obtusifolia), signalgrass (Brachiaria platyphylla),smartweed (Polygonum pericaria), teaweed (Sida spinosa), and velvetleaf(Abutilon theophrasti) and purple nutsedge (Cyperus rotundus) tuberswere planted and treated preemergence with test chemicals dissolved in anon-phytotoxic solvent. Treated plants and controls were maintained in agreenhouse for approximately 21 days, after which all species werecompared to controls and visually elevated. Response ratings, summarizedin Table E, are based on a scale of 0 to 100 where 0 is no effect and100 is complete control. A dash (-) response means no test result.

                                      TABLE E                                     __________________________________________________________________________    PREEMERGENCE                                                                  __________________________________________________________________________             Cmpd 13            Cmpd 15            Cmpd 23                        RATE (g/ha)                                                                            1000                                                                              500                                                                              250                                                                              125                                                                              64 32 1000                                                                              500                                                                              250                                                                              125                                                                              64 32 1000                                                                              500                                                                              250                                                                              125                                                                              64                __________________________________________________________________________    Barnyardgrass                                                                          100 100                                                                              98 40 20 10 100 100                                                                              60 90 20 10 100 100                                                                              100                                                                              70 30                Bermudagrass                                                                           100 100                                                                              0  0  0  0  90  40 30 20 0  0  100 100                                                                              100                                                                              60 20                Cocklebur                                                                              40  0  0  0  0  0  0   0  0  0  0  0  0   0  0  0  0                 Cotton   5   0  0  0  0  0  10  0  0  0  0  0  10  0  0  0  0                 Fall Panicum                                                                           --  -- -- -- -- -- --  -- -- -- -- -- 100 100                                                                              100                                                                              100                                                                              100               Goosegrass                                                                             100 98 70 60 50 30 100 100                                                                              100                                                                              98 70 50 100 100                                                                              100                                                                              80 40                Ground cherry                                                                          100 100                                                                              40 20 0  0  100 98 50 40 20 10 100 100                                                                              60 30 20                Johnsongrass                                                                           100 60 30 0  0  0  100 100                                                                              50 0  0  0  80  60 30 20 0                 Lambsquarters                                                                          100 100                                                                              100                                                                              90 70 0  100 100                                                                              100                                                                              100                                                                              90 0  --  -- -- -- --                Large crabgrass                                                                        100 100                                                                              100                                                                              95 70 60 100 100                                                                              100                                                                              100                                                                              70 30 100 100                                                                              100                                                                              100                                                                              90                Morningglory                                                                           100 100                                                                              70 20 0  0  100 100                                                                              40 20 0  0  100 90 100                                                                              20 0                 Nutsedge 100 50 50 20 0  0  90  50 50 0  -- -- 30  40 30 20 10                Purslane 100 100                                                                              100                                                                              100                                                                              90 0  100 100                                                                              100                                                                              100                                                                              100                                                                              20 100 100                                                                              100                                                                              100                                                                              100               Redroot pigweed                                                                        100 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              95 100 100                                                                              100                                                                              100                                                                              100               Sicklepod                                                                              60  20 0  0  0  0  100 70 0  0  0  0  100 100                                                                              80 30 0                 Signalgrass                                                                            --  -- -- -- -- -- --  -- -- -- -- -- 100 100                                                                              100                                                                              90 20                Smartweed                                                                              100 20 10 0  0  0  100 30 0  0  0  0  100 50 0  0  0                 Teaweed  100 100                                                                              50 0  0  0  100 100                                                                              30 0  0  0  100 100                                                                              100                                                                              60 0                 Velvetleaf                                                                             100 100                                                                              50 0  0  0  100 100                                                                              60 10 0  0  100 100                                                                              98 98 30                __________________________________________________________________________                                 Cmpd 25          Cmpd 32                                             RATE (g/ha)                                                                            1000                                                                              500                                                                              250 125                                                                              64 1000                                                                              500                                                                              250 125                                                                              64                __________________________________________________________________________                        Barnyardgrass                                                                          100 100                                                                              100 20 10 100 100                                                                              100 100                                                                              0                                     Bermudagrass                                                                           100 100                                                                              60  20 20 100 100                                                                              95  95 20                                    Cocklebur                                                                              0   0  0   0  0  0   0  0   0  0                                     Cotton   5   5  0   0  0  0   0  0   0  0                                     Fall Panicum                                                                           100 100                                                                              100 100                                                                              30 --  -- --  -- --                                    Goosegrass                                                                             100 100                                                                              100 80 50 100 100                                                                              100 100                                                                              50                                    Ground cherry                                                                          95  70 20  10 0  100 100                                                                              60  50 0                                     Johnsongrass                                                                           70  30 20  0  0  30  30 30  20 0                                     Lambsquarters                                                                          --  -- --  -- -- --  -- --  -- --                                    Large crabgrass                                                                        100 100                                                                              100 95 85 100 100                                                                              100 100                                                                              50                                    Morningglory                                                                           100 95 30  30 0  100 70 60  0  0                                     Nutsedge 30  10 0   0  0  10  10 0   0  0                                     Purslane 100 100                                                                              100 100                                                                              90 --  -- --  -- --                                    Redroot pigweed                                                                        100 100                                                                              100 100                                                                              100                                                                              100 100                                                                              100 100                                                                              70                                    Sicklepod                                                                              100 70 20  10 0  --  -- --  -- --                                    Signalgrass                                                                            100 100                                                                              60  60 20 100 100                                                                              100 100                                                                              0                                     Smartweed                                                                              70  20 0   0  0  100 20 20  0  0                                     Teaweed  100 70 40  20 0  100 100                                                                              100 90 90                                    Velvetleaf                                                                             100 80 50  30 20 90  60 60  30 0                 __________________________________________________________________________                                 Cmpd 50          Cmpd 53                                             RATE (g/ha)                                                                            500                                                                              250                                                                              125                                                                              64 32 16                                                                              500                                                                              250                                                                              125                                                                              64 32 16               __________________________________________________________________________                        Barnyardgrass                                                                          100                                                                              90 80 30 0  0 100                                                                              70 60 30 20 0                                    Bermudagrass                                                                           100                                                                              60 60 30 30 30                                                                              100                                                                              100                                                                              100                                                                              95 30 10                                   Cocklebur                                                                              0  0  0  0  0  0 50 0  0  0  0  0                                    Cotton   20 20 10 0  0  0 20 10 0  0  0  0                                    Fall Panicum                                                                           100                                                                              100                                                                              100                                                                              90 90 0 100                                                                              100                                                                              100                                                                              50 50 0                                    Goosegrass                                                                             100                                                                              100                                                                              100                                                                              70 40 40                                                                              100                                                                              90 80 50 10 10                                   Ground cherry                                                                          100                                                                              90 80 30 10 0 100                                                                              100                                                                              40 40 10 0                                    Johnsongrass                                                                           100                                                                              100                                                                              60 10 10 0 100                                                                              100                                                                              100                                                                              95 80 0                                    Lambsquarters                                                                          100                                                                              100                                                                              100                                                                              50 50 0 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              0                                    Large crabgrass                                                                        100                                                                              100                                                                              100                                                                              100                                                                              95 95                                                                              100                                                                              100                                                                              100                                                                              100                                                                              70 40                                   Morningglory                                                                           90 70 20 0  0  0 100                                                                              100                                                                              30 0  0  0                                    Nutsedge 30 20 10 0  0  0 20 20 20 10 0  0                                    Purslane -- -- -- -- -- --                                                                              -- -- -- -- -- --                                   Redroot pigweed                                                                        100                                                                              100                                                                              100                                                                              100                                                                              20 0 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              30                                   Sicklepod                                                                              100                                                                              0  60 0  0  0 100                                                                              100                                                                              100                                                                              50 -- --                                   Signalgrass                                                                            100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              90                                                                              100                                                                              100                                                                              100                                                                              95 60 20                                   Smartweed                                                                              100                                                                              60 0  0  0  0 100                                                                              100                                                                              70 100                                                                              0  --                                   Teaweed  80 100                                                                              70 50 50 50                                                                              100                                                                              100                                                                              100                                                                              100                                                                              0  0                                    Velvetleaf                                                                             90 70 40 0  0  0 100                                                                              80 70 40 0  0                __________________________________________________________________________

TEST F

Seeds of barnyardgrass (Echinochloa crus-galli), black nightshade(Solanum nigrum), cocklebur (Xanthium pensylvanicum), corn (Zea mays),fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberi),green foxtail (Setaria viridis), hemp sesbania (Sesbania exaltata),jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense),lambsquarters (Chenopodium album), large crabgrass. (Digitariasanguinalis), morningglory (Ipomoea hederacea), redroot pigweed(Amaranthus retroflexus), sicklepod (Cassia obtusifolia), signalgrass(Brachiaria platyphylla), smartweed (Polygonum persicaria), soybean(Glycine max), teaweed (Sida spinosa), and velvetleaf (Abutilontheophrasti) and purple nutsedge (Cyperus rotundus) tubers were plantedin a silt loam soil and treated preemergence with test chemicalsdissolved in a non-phytotoxic solvent. Treated plants and controls weremaintained in a greenhouse for approximately 21 days, after which allspecies were compared to controls and visually evaluated. Responseratings, summarized in Table F, are based on a scale of 0 to 100 where 0is no effect and 100 is complete control. A dash (-) response means notest result.

                                      TABLE F                                     __________________________________________________________________________    PREEMERGENCE                                                                  __________________________________________________________________________             Cmpd 13        Cmpd 15                                               RATE (g/ha)                                                                            1000                                                                             500                                                                              250                                                                              125                                                                              64 1000                                                                             500                                                                              250                                                                              125                                                                              64                                        __________________________________________________________________________    Barnyardgrass                                                                          100                                                                              70 20 0  0  100                                                                              95 70 0  0                                         Black nightshade                                                                       100                                                                              20 0  0  0  100                                                                              75 60 40 20                                        Cocklebur                                                                              30 20 0  0  0  50 30 0  0  0                                         Corn     40 15 10 0  0  45 45 0  0  0                                         Fall panicum                                                                           -- -- -- -- -- -- -- -- -- --                                        Giant foxtail                                                                          100                                                                              100                                                                              100                                                                              100                                                                              20 100                                                                              100                                                                              100                                                                              85 85                                        Green foxtail                                                                          100                                                                              100                                                                              100                                                                              70 30 100                                                                              100                                                                              100                                                                              95 80                                        Hemp sesbania                                                                          100                                                                              70 30 0  0  100                                                                              85 40 40 20                                        Jimsonweed                                                                             100                                                                              20 0  0  0  100                                                                              80 40 0  0                                         Johnsongrass                                                                           45 20 0  0  0  80 45 20 0  0                                         Lambsquarters                                                                          100                                                                              100                                                                              98 98 30 100                                                                              100                                                                              100                                                                              100                                                                              98                                        Large crabgrass                                                                        100                                                                              100                                                                              100                                                                              70 0  100                                                                              100                                                                              100                                                                              85 70                                        Morningglory                                                                           100                                                                              70 0  0  0  100                                                                              75 75 0  0                                         Nutsedge 75 50 0  0  0  80 80 80 0  0                                         Redrood pigweed                                                                        100                                                                              100                                                                              100                                                                              100                                                                              95 100                                                                              100                                                                              100                                                                              100                                                                              100                                       Sicklepod                                                                              30 0  0  0  0  20 0  0  0  0                                         Signalgrass                                                                            100                                                                              100                                                                              100                                                                              80 70 100                                                                              100                                                                              100                                                                              80 70                                        Smartweed                                                                              30 0  0  0  0  60 50 40 0  0                                         Soybean  90 30 10 0  0  65 65 0  0  0                                         Teaweed  30 0  0  0  0  30 0  0  0  0                                         Velvetleaf                                                                             100                                                                              80 30 0  0  100                                                                              100                                                                              60 30 0                                         __________________________________________________________________________             Cmpd 23        Cmpd 25                                               RATE (g/ha)                                                                            1000                                                                             500                                                                              250                                                                              125                                                                              64 1000                                                                             500                                                                              250                                                                              125                                                                              64                                        __________________________________________________________________________    Barnyardgrass                                                                          100                                                                              100                                                                              80 60 40 100                                                                              100                                                                              70 40 0                                         Black nightshade                                                                       100                                                                              100                                                                              85 40 0  100                                                                              100                                                                              100                                                                              70 0                                         Cocklebur                                                                              50 50 20 0  0  100                                                                              40 20 0  0                                         Corn     75 60 40 20 0  50 30 0  0  0                                         Fall panicum                                                                           -- -- -- -- -- 100                                                                              100                                                                              100                                                                              100                                                                              0                                         Giant foxtail                                                                          100                                                                              100                                                                              100                                                                              100                                                                              90 100                                                                              100                                                                              100                                                                              100                                                                              0                                         Green foxtail                                                                          100                                                                              100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              100                                                                              98 0                                         Hemp sesbania                                                                          100                                                                              100                                                                              80 40 20 100                                                                              100                                                                              100                                                                              70 0                                         Jimsonweed                                                                             100                                                                              100                                                                              70 30 0  100                                                                              100                                                                              40 20 0                                         Johnsongrass                                                                           100                                                                              75 60 40 0  98 75 50 30 0                                         Lambsquarters                                                                          100                                                                              100                                                                              100                                                                              100                                                                              98 100                                                                              100                                                                              100                                                                              100                                                                              0                                         Large crabgrass                                                                        100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              0                                         Morningglory                                                                           100                                                                              100                                                                              75 50 0  100                                                                              100                                                                              30 0  0                                         Nutsedge 90 50 50 50 0  0  0  0  0  0                                         Redrood pigweed                                                                        100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              30                                        Sicklepod                                                                              85 40 0  0  0  40 20 0  0  0                                         Signalgrass                                                                            100                                                                              100                                                                              100                                                                              100                                                                              90 100                                                                              100                                                                              95 70 0                                         Smartweed                                                                              75 50 20 0  0  100                                                                              60 30 0  0                                         Soybean  100                                                                              75 40 20 0  45 20 0  0  0                                         Teaweed  100                                                                              85 30 0  0  80 80 30 0  0                                         Velvetleaf                                                                             100                                                                              100                                                                              100                                                                              70 50 100                                                                              98 50 40 0                                         __________________________________________________________________________

TEST G

Seeds of barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthiumpensylvanicum), corn (Zea mays), crabgrass (Digitaria spp.), fallpanicum (Panicum dichotomiflorum), giant foxtail (Setaria faberi), greenfoxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass(Sorghum halepense), lambsquarters (Chenopodium album), morningglory(Ipomoea hederacea), redroot pigweed (Amaranthus retroflexus), smartweed(Polygonum persicaria), sorghum (Sorghum bicolor), soybean (Glycinemax), and velvetleaf (Abutilon theophrasti) and purple nutsedge (Cyperusrotundus) tubers were planted and treated preemergence with testchemicals dissolved in a non-phytotoxic solvent. Several of the testcompounds were also applied postemergence to these crop and weedspecies. For postemergence applications, plants were from two totwenty-five cm tall.

The soil surface of an additional container of corn (Corn, Perlite) tobe treated postemergence was covered with the absorbent, perlite, beforepostemergence treatments were applied. After application of testcompounds, the perlite was removed from the soil surface to removechemical sorbed onto the perlite. This procedure would therefore allowonly that portion of chemical sorbed onto the plant foliage to causecorn injury response.

Treated plants and controls were maintained in a greenhouse forapproximately 24 days, after which all species were compared to controlsand visually evaluated. Test rates for each compound are listed in TableG. The ratings, summarized in Table G, are based on a scale of 0 to 100where 0 is no effect and 100 is complete control. A dash (-) responsemeans no test result.

                                      TABLE G                                     __________________________________________________________________________    POSTEMERGENCE                                                                          Cmpd 5        Cmpd 13    Cmpd 15                                     RATE (g/ha)                                                                            1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              500                                                                              250                                                                              125                                                                              64                                                                              1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              32                                                                              16                          __________________________________________________________________________    Barnyardgrass                                                                          70 35 20 0  0 20 0  0       65 50 45 40                                                                              30                                                                              25                          Cocklebur                                                                              35 25 0  0  0 45 25 0       45 40 30 25                                                                              0 0                           Corn     40 20 0  0  0 0  0  0       40 0  0  0 0 0                           Corn (Perlite)                                                                         25 0  0  0  0 0  0  0       30 0  0  0 0 0                           Crabgrass                                                                              80 50 35 0  0 0  0  0       70 55 45 40                                                                              30                                                                              20                          Fall panicum                                                                           45 20 0  0  0 0  0  0       60 45 40 35                                                                              25                                                                              0                           Giant foxtail                                                                          35 0  0  0  0 25 0  0       60 45 40 30                                                                              25                                                                              20                          Green foxtail                                                                          60 25 0  0  0 35 0  0       -- -- -- --                                                                              --                                                                              --                          Jimsonweed                                                                             100                                                                              95 85 45 0 -- 25 0       85 75 50 45                                                                              40                                                                              25                          Johnsongrass                                                                           40 25 0  0  0 20 0  0       65 55 50 45                                                                              40                                                                              30                          Lambsquarters                                                                          -- -- -- -- --                                                                              -- -- --      95 80 65 55                                                                              45                                                                              30                          Morningglory                                                                           65 40 35 20 0 45 20 0       60 50 40 35                                                                              25                                                                              0                           Nutsedge 0  0  0  0  0 0  0  0       20 0  0  0 0 0                           Redroot pigweed                                                                        100                                                                              100                                                                              95 75 35                                                                              -- 50 0       95 80 55 40                                                                              40                                                                              25                          Smartweed                                                                              40 25 0  0  0 -- -- --      65 50 35 30                                                                              20                                                                              0                           Sorghum  45 20 0  0  0 20 0  0       65 55 50 45                                                                              35                                                                              25                          Soybean  85 65 40 20 0 50 35 0       60 40 35 30                                                                              20                                                                              0                           Velvetleaf                                                                             55 25 20 0  0 50 35 0       60 50 40 30                                                                              20                                                                              0                           __________________________________________________________________________    PREEMERGENCE                                                                           Cmpd 5        Cmpd 13    Cmpd 15                                     RATE (g/ha)                                                                            1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              500                                                                              250                                                                              125                                                                              64                                                                              1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              32                                                                              16                          __________________________________________________________________________    Barnyardgrass                                                                          75 45 25 0    100                                                                              85 45 20                                                                              100                                                                              100                                                                              55 25 0 0 0                           Cocklebur                                                                              0  0  0  0    0  0  0  0 25 0  0  0  0 0 0                           Corn     25 0  0  0    0  0  0  0 40 20 0  0  0 0 0                           Corn (Perlite)                                                                Crabgrass                                                                              65 40 20 0    100                                                                              100                                                                              65 20                                                                              100                                                                              100                                                                              85 40 0 0 0                           Fall panicum                                                                           50 35 0  0    100                                                                              80 35 0 100                                                                              100                                                                              65 35 0 0 0                           Giant foxtail                                                                          20 0  0  0    100                                                                              95 60 30                                                                              95 90 60 25 0 0 0                           Green foxtail                                                                          45 25 0  0    100                                                                              90 65 30                                                                              100                                                                              100                                                                              70 35 0 0 0                           Jimsonweed                                                                             100                                                                              75 35 0    25 0  0  0 100                                                                              100                                                                              70 35 0 0 0                           Johnsongrass                                                                           55 40 20 0    95 85 50 20                                                                              95 75 40 20 0 0 0                           Lambsquarters                                                                          100                                                                              100                                                                              65 40   -- -- -- --                                                                              100                                                                              100                                                                              90 45 0 0 0                           Morningglory                                                                           40 0  0  0    0  0  0  0 95 90 50 20 0 0 0                           Nutsedge 0  0  0  0    0  0  0  0 25 0  0  0  0 0 0                           Redroot pigweed                                                                        100                                                                              100                                                                              70 40   100                                                                              100                                                                              60 20                                                                              100                                                                              100                                                                              90 40 0 0 0                           Smartweed                                                                              55 35 20 0    -- -- -- --                                                                              100                                                                              95 65 30 0 0 0                           Sorghum  20 0  0  0    20 0  0  0 50 25 0  0  0 0 0                           Soybean  40 0  0  0    50 20 0  0 55 30 0  0  0 0 0                           Velvetleaf                                                                             100                                                                              60 25 0    40 25 0  0 100                                                                              90 50 20 0 0 0                           __________________________________________________________________________    PREEMERGENCE                                                                           Cmpd 23               Cmpd 32                                        RATE (g/ha)                                                                            1000                                                                             500 250                                                                              125 64 32 16                                                                              1000                                                                              500                                                                              250 125                                                                              64  32                           __________________________________________________________________________    Barnyardgrass                                                                          100                                                                              100 100                                                                              100 65 35 0 100 95 65  40 20  0                            Cocklebur                                                                              20 0   0  0   0  0  0 0   0  0   0  0   0                            Corn     65 50  30 0   0  0  0 65  45 20  0  0   0                            Corn (Perlite)                                                                Crabgrass                                                                              100                                                                              100 100                                                                              100 100                                                                              75 25                                                                              100 100                                                                              90  60 30  0                            Fall panicum                                                                           100                                                                              100 100                                                                              100 45 20 0 100 70 55  30 20  0                            Giant foxtail                                                                          100                                                                              100 100                                                                              100 100                                                                              50 20                                                                              100 85 60  20 0   0                            Green foxtail                                                                          100                                                                              100 100                                                                              100 90 35 0 100 90 70  40 25  0                            Jimsonweed                                                                             100                                                                              100 100                                                                              100 75 30 0 100 85 35  20 0   0                            Johnsongrass                                                                           100                                                                              100 90 70  50 20 0 95  90 65  35 25  0                            Lambsquarters                                                                          -- --  -- --  -- -- --                                                                              100 100                                                                              100 100                                                                              95  55                           Morningglory                                                                           100                                                                              100 85 40  0  0  0 100 90 60  35 0   0                            Nutsedge 45 35  20 0   0  0  0 25  0  0   0  0   0                            Redroot pigweed                                                                        100                                                                              100 100                                                                              100 100                                                                              90 40                                                                              100 100                                                                              100 100                                                                              100 60                           Smartweed                                                                              100                                                                              100 95 75  60 25 0 80  65 50  45 35  25                           Sorghum  75 60  30 0   0  0  0 60  35 20  0  0   0                            Soybean  100                                                                              80  65 25  0  0  0 85  65 35  20 0   0                            Velvetleaf                                                                             100                                                                              100 85 65  20 0  0 95  65 25  0  0   0                            __________________________________________________________________________                       PREEMERGENCE                                                                           Cmpd 36      Cmpd 50                                                 RATE (g/ha)                                                                            500                                                                              250                                                                              125                                                                              64                                                                              32                                                                              250                                                                              125                                                                              64 32                          __________________________________________________________________________                       Barnyardgrass                                                                          100                                                                              100                                                                              70 30                                                                              0 100                                                                              85 75 30                                             Cocklebur                                                                              0  0  0  0 0 0  0  0  0                                              Corn     65 40 30 0 0 45 25 0  0                                              Corn (Perlite)                                                                Crabgrass                                                                              100                                                                              100                                                                              95 65                                                                              35                                                                              100                                                                              100                                                                              80 35                                             Fall panicum                                                                           100                                                                              100                                                                              40 20                                                                              0 95 70 50 0                                              Giant foxtail                                                                          100                                                                              85 35 0 0 100                                                                              80 55 20                                             Green foxtail                                                                          100                                                                              100                                                                              65 30                                                                              0 100                                                                              95 65 35                                             Jimsonweed                                                                             100                                                                              90 35 0 0 65 40 0  0                                              Johnsongrass                                                                           80 75 40 0 0 85 80 50 20                                             Lambsquarters                                                                          100                                                                              100                                                                              100                                                                              70                                                                              40                                                                              100                                                                              90 85 60                                             Morningglory                                                                           100                                                                              40 30 0 0 65 45 20 0                                              Nutsedge 40 20 0  0 0 20 0  0  0                                              Redroot pigweed                                                                        100                                                                              100                                                                              100                                                                              90                                                                              60                                                                              100                                                                              100                                                                              100                                                                              70                                             Smartweed                                                                              60 55 40 20                                                                              0 60 40 25 0                                              Sorghum  60 40 0  0 0 55 35 0  0                                              Soybean  65 35 25 0 0 40 20 0  0                                              Velvetleaf                                                                             90 45 25 0 0 60 40 0  0                           __________________________________________________________________________

TEST H

Seeds of blackgrass (Alopercurus myosuroides), catchweed bedstraw(Galium aparine) , chickweed (Stellaria media), knotweed (Polygonumaviculare), lambsquarters (Chenopodium album(, Persian speedwell(Veronica persica), scentless chamomile (Viola arvensis), sugar beet(Beta vulgaris), viola (Viola arvensis), wheat (Triticum aestivum), wildbuckwheat (Polygonum convolvulus), and wild oat (Avena fatua), wereplanted and treated preemergence with test chemicals dissolved in anon-Phytotoxic solvent. These crop and weed species were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to twenty cm (two to three leaf stage) for postemergencetreatments. Treated plants and controls were maintained in a greenhousefor approximately 24 days, after which all species were compared tocontrols and visually evaluated. Application rates for each testchemical are shown in Table H. Plant response ratings, summarized inTable H, are based on a scale of 0 to 100 where 0 is no effect and 100is complete control. A dash (-) response means no test result.

                                      TABLE H                                     __________________________________________________________________________    POSTEMERGENCE                                                                            Cmpd 28        Cmpd 36        Cmpd 71                              RATE (g/ha)                                                                              1000                                                                             750                                                                              500                                                                              250                                                                              125                                                                              2000                                                                             1500                                                                             1000                                                                             500                                                                              250                                                                              250                                                                              125                                                                              64 32                                                                              16                        __________________________________________________________________________    Blackgrass    20 20 0  0  100                                                                              100                                                                              100                                                                              80 20          30                                                                              0                         Catchweed bedstraw                                                                          30 30 0  0  100                                                                              100                                                                              100                                                                              100                                                                              100         0 0                         Chickweed     0  0  0  0  100                                                                              90 80 80 80          30                                                                              20                        Knotweed      100                                                                              100                                                                              100                                                                              70 -- -- -- -- --          --                                                                              --                        Lambsquarters 90 90 50 50 100                                                                              100                                                                              100                                                                              100                                                                              100         60                                                                              50                        Persian speedwell                                                                           100                                                                              100                                                                              100                                                                              70 100                                                                              100                                                                              100                                                                              80 80          80                                                                              60                        Scentless chamomille                                                                        30 0  0  0  80 80 70 50 30          0 0                         Sugar beet    20 20 0  0  100                                                                              100                                                                              100                                                                              90 80          50                                                                              35                        Viola         80 50 50 0  100                                                                              100                                                                              100                                                                              100                                                                              100         80                                                                              50                        Wheat         0  0  0  0  10 10 10 10 10          30                                                                              0                         Wild buckwheat                                                                              50 50 20 0  100                                                                              100                                                                              100                                                                              90 80          20                                                                              0                         Wild oat      0  0  0  0  50 50 50 30 30          0 0                         __________________________________________________________________________    PREEMERGENCE                                                                             Cmpd 28        Cmpd 36        Cmpd 68                              RATE (g/ha)                                                                              1000                                                                             750                                                                              500                                                                              250                                                                              125                                                                              2000                                                                             1500                                                                             1000                                                                             500                                                                              250                                                                              125                                                                              64 32                                                                              16                                                                              8 4                        __________________________________________________________________________    Blackgrass 50 50 30 30 0           100                                                                              80 40 20 20                                                                              20                                                                              0 0                        Catchweed bedstraw                                                                       90 70 70 30 0           95 70 0  0  0 0 0 0                        Chickweed  20 20 0  0  0           100                                                                              100                                                                              100                                                                              60 50                                                                              0 0 0                        Knotweed   100                                                                              100                                                                              100                                                                              30 0           -- -- -- -- --                                                                              --                                                                              --                                                                              --                       Lambsquarters                                                                            100                                                                              80 80 80 0           100                                                                              100                                                                              100                                                                              100                                                                              90                                                                              60                                                                              50                                                                              30                       Persian speedwell                                                                        90 80 50 50 0           100                                                                              100                                                                              100                                                                              90 30                                                                              0 0 0                        Scentless chamomille                                                                     80 70 70 70 30          -- -- -- -- --                                                                              --                                                                              --                                                                              --                       Sugar beet 0  0  0  0  0           100                                                                              100                                                                              100                                                                              50 50                                                                              40                                                                              20                                                                              10                       Viola      90 50 30 20 0           100                                                                              100                                                                              30 20 20                                                                              0 0 0                        Wheat      20 0  0  0  0           30 20 30 20 20                                                                              10                                                                              0 0                        Wild buckwheat                                                                           80 80 40 40 20          100                                                                              100                                                                              90 50 30                                                                              20                                                                              0 0                        Wild oat   30 30 30 30 0           70 50 0  0  0 0 0 0                        __________________________________________________________________________                                    PREEMERGENCE                                                                             Cmpd 71                                                            RATE (g/ha)                                                                              250                                                                              125                                                                              64                                                                              32                                                                              16                       __________________________________________________________________________                                    Blackgrass 80 80 75                                                                              0 0                                                        Catchweed bedstraw                                                                       0  0  0 0 0                                                        Chickweed  100                                                                              90 0 0 0                                                        Knotweed   -- -- --                                                                              --                                                                              --                                                       Lambsquarters                                                                            100                                                                              70 70                                                                              50                                                                              30                                                       Persian speedwell                                                                        50 40 30                                                                              20                                                                              0                                                        Scentless chamomille                                                                     -- -- --                                                                              0 0                                                        Sugar beet 100                                                                              90 60                                                                              50                                                                              30                                                       Viola      90 60 50                                                                              20                                                                              20                                                       Wheat      30 30 20                                                                              0 0                                                        Wild buckwheat                                                                           100                                                                              70 30                                                                              20                                                                              0                                                        Wild oat   20 20 0 0 0                        __________________________________________________________________________

TEST I

Seeds of alfalfa (Medicago sativa), barley (Hordeum vulgare), bluegrass(Poa pratensis), corn (Zea mays), cotton (Gossypium hirsutum), flax(Linum usitatissimum), oat (Avena sativa), pea (sativum), peanut(Arachis hypogaea), rape (Brassica napus), rice (Oryza sativa), sorghum(Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris),sunflower (Helianthus annuus), tomato (Lycopersicon esculentum), andwheat (Triticum aeastivum), were planted and treated preemergence with atest chemical dissolved in a non-phytotoxic solvent. These crop specieswere also treated with postemergence applications of the test chemical.Plants ranged in height from four to twenty cm (two to three leaf stage)when post-emergence applications were applied. Treated plants andcontrols were grown under greenhouse conditions for approximatelytwenty-four days, after which all plants treated with the test chemicalwere compared to untreated controls and visually evaluated for injuryresponse. Application rates for the test chemical are shown in Table I.Plant response ratings, summarized in Table I, are from 0 to 100 where 0is no injury and 100 is complete control. A dash (-) response means notest result.

                                      TABLE I                                     __________________________________________________________________________    POSTEMERGENCE                                                                        Cmpd 15         Cmpd 23                                                RATE (g/ha)                                                                          1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              32                                                                              2000                                                                             1000                                                                             500                                                                              250                                                                              125                                        __________________________________________________________________________    Alfalfa                                                                              100                                                                              95 60 30 0      95 70 50 25                                         Barley 80 35 20 0  0      80 40 25 0                                          Bluegrass                                                                            90 75 30 0  0      95 60 35 0                                          Corn   75 40 20 0  0      90 65 40 20                                         Cotton 100                                                                              85 60 30 0      60 40 20 0                                          Flax   70 50 40 20 0      -- -- -- --                                         Oat    80 40 20 0  0      95 60 30 0                                          Pea    100                                                                              100                                                                              80 70 35     80 55 35 20                                         Peanut 100                                                                              85 70 40 20     100                                                                              70 40 20                                         Rape   100                                                                              95 70 50 25     100                                                                              90 55 20                                         Rice   95 70 20 0  0      85 65 40 0                                          Sorghum                                                                              75 40 20 0  0      85 65 40 15                                         Soybean                                                                              95 85 65 40 25     95 75 55 25                                         Sugar beet                                                                           100                                                                              100                                                                              75 60 35     100                                                                              100                                                                              65 35                                         Sunflower                                                                            100                                                                              90 75 50 35     -- -- -- --                                         Tomato 100                                                                              100                                                                              80 65 25     100                                                                              85 60 20                                         Wheat  80 40 25 0  0      85 50 25 0                                          __________________________________________________________________________    PREEMERGENCE                                                                         Cmpd 15         Cmpd 23                                                RATE (g/ha)                                                                          1000                                                                             500                                                                              250                                                                              125                                                                              64                                                                              32                                                                              2000                                                                             1000                                                                             500                                                                              250                                                                              125                                        __________________________________________________________________________    Alfalfa                                                                              100                                                                              100                                                                              70 45 25                                                                              0 100                                                                              100                                                                              100                                                                              70 35                                         Barley 85 40 0  0  0 0 100                                                                              100                                                                              90 40 20                                         Bluegrass                                                                            100                                                                              100                                                                              80 45 25                                                                              0 100                                                                              100                                                                              100                                                                              95 65                                         Corn   90 65 30 0  0 0 100                                                                              100                                                                              95 65 30                                         Cotton 35 0  0  0  0 0 30 20 0  0  0                                          Flax   100                                                                              85 50 35 0 0 100                                                                              100                                                                              100                                                                              80 40                                         Oat    95 85 60 40 25                                                                              0 100                                                                              100                                                                              95 45 25                                         Pea    100                                                                              70 35 0  0 0 100                                                                              100                                                                              75 30 0                                          Peanut 85 55 30 0  0 0 95 65 50 20 0                                          Rape   100                                                                              100                                                                              100                                                                              75 40                                                                              20                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Rice   60 30 0  0  0 0 100                                                                              100                                                                              90 60 35                                         Sorghum                                                                              100                                                                              95 80 40 20                                                                              0 100                                                                              100                                                                              95 65 35                                         Soybean                                                                              95 70 35 0  0 0 100                                                                              95 85 50 25                                         Sugar beet                                                                           100                                                                              100                                                                              100                                                                              75 45                                                                              20                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Sunflower                                                                            80 50 30 0  0 0 95 60 50 20 0                                          Tomato 100                                                                              100                                                                              65 25 0 0 100                                                                              100                                                                              100                                                                              100                                                                              70                                         Wheat  85 40 0  0  0 0 100                                                                              100                                                                              85 40 25                                         __________________________________________________________________________

What is claimed is:
 1. A compound of the formula ##STR27## wherein G is C;G¹ is N; R₁ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, halogen, C₂ -C₄ alkylcarbonyl, C₁ -C₄ alkylamino, C₂ -C₄ dialkylamino or C₂ -C₄ alkylthioalkyl; R₂ is halogen, NO₂, OR₃, S(O)_(n) R₃ OSO₂ R₃, C₁ -C₄ haloalkyl, C₃ -C₄ halocycloalkyl, C₃ -C₄ haloalkynyl or C₂ -C₄ haloalkenyl; R₃ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₃ -C₄ alkynyl, C₃ -C₄ haloalkynyl, or C₃ C-₄ halocycloalkyl; R₄ is H, halogen, C₁ -C₃ alkoxy, C₁ -C₃ alkyl or CF₃ ; R₅ is H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl, NO₂, OR₃, S(O)_(n) R₃, OSO₂ R₃, phenyl, phenoxy, C₂ -C₄ alkoxycarbonyl, C₂ -C₄ alkylcarbonyl, CN, NHSO₂ CF₃, C₂ -C₄ haloalkenyl, C₃ -C₄ haloalkynyl, C₂ -C₄ dialkylamino or C₃ -C₄ halocycloalkyl; n is 0, 1 or 2; R₆ is H or F; X, Y and Z are N; and R₇ is H, CN, halogen, NO₂, CO₂ R₃, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl or CONH₂.
 2. A compound of claim 1 whereinFormula I is Ia; X is N; Y is N; and Z is N.
 3. A compound of claim 2 whereinR₆ is H; and R₁ is C₁ -C₃ alkyl, SCH₃, NHCH₃, CH₂ OCH₃ or CH₂ SCH₃.
 4. Compounds of claim 3 whereinR₂ is CF₃, SCF₃, SCF₂ H, OCF₃,OCH₂ CHF₂, OCH₂ CF₃, OCF₂ H, CF₂ CF₃, CF₂ Cl, CHF₂, CH═CF₂ or 2, 2-difluorocyclopropane;
 5. Compounds of claim 4 whereinR₃ is CH₂ CH₂ F, CH₂ CF₃, CH(CH₃)CF₃, CH₂ CH₂ CF₃, CH₂ CHF₂, CF₃ or CF₂ H; and R₄ is H.
 6. Compounds of claim 5 whereinR₅ is H, halogen, OCH₃, OCF₂ H, OCH₂ CF₃, SCF₃, C₁ -C₃ alkyl, OCF₃, OCH₂ CHF₂, OCH₂ CF₃, OCH₂ CH₂ F, SCHF₂, CF₃, CHF₂, CF₂ Cl, CH₂ CF₃, CH₂ F, CCl₃, CH₂ Cl or CN and R₅ is in the meta position.
 7. Compounds of claim 6 whereinR₁ is C₁ -C₃ alkyl.
 8. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of any one of claim 1, 2 and 3 through 7 and at least one of the following: surfactant, solid diluent or liquid diluent.
 9. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of any one of claim 1, 2 and 3 through
 7. 10. The method of claim 9 wherein the undesired vegetation is present in wheat or barley. 